66356-53-4

Basic information

• Product Name: 5-[[(2-Aminoethyl)thio]methyl]-N,N-dimethyl-2-furfurylamine
• Synonyms: RANITIDINE IMPURITY B;N,N-DIMETHYL-5-(2-AMINOETHYLTHIOMETHYL)FURFURYLAMINE;N-[(5-([(2-AMINOETHYL)SULFANYL]METHYL)-2-FURYL)METHYL]-N,N-DIMETHYLAMINE;2-(5-DIMETHYLAMINOMETHYL-FURAN-2-YLMETHYLSULFANYL)-ETHYLAMINE;2-([(5-DIMETHYLAMINO)METHYLFURFURYL]THIO) ETHYLAMINE;[2-[(5-DIMETHYLAMINO)METHYLFURYL]THIO]ETHYLAMINE;2-[((5-[(DIMETHYLAMINO)METHYL]-2-FURYL)METHYL)THIO]ETHAN-1-AMINE;2-[[[5-(DIMETHYLAMINE)METHYL-2-FURYL]METHYL]THIO]ETHANAMINE
• CAS NO: 66356-53-4
• Molecular Formula: C10H18N2OS
• Molecular Weight: 214.33
• EINECS: 266-330-4
• Product Categories: Sulphur Derivatives;Furans, Benzofurans & Dihydrobenzofurans;Amines;Heterocycles;Metabolites & Impurities;Sulfur & Selenium Compounds;Furans, Benzofurans & Dihydrobenzofurans
• Mol File: 66356-53-4.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 106°C/0.1mmHg(lit.)
• Flash Point: 130.9 °C
• Appearance: Light yellow or brown liquid
• Density: 1.094 g/cm³
• Vapor Pressure: 0.00179mmHg at 25°C
• Refractive Index: 1.5300 to 1.5340
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Ethyl Acetate
• PKA: 8.93±0.10(Predicted)
• CAS DataBase Reference: 5-[[(2-Aminoethyl)thio]methyl]-N,N-dimethyl-2-furfurylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[[(2-Aminoethyl)thio]methyl]-N,N-dimethyl-2-furfurylamine(66356-53-4)
• EPA Substance Registry System: 5-[[(2-Aminoethyl)thio]methyl]-N,N-dimethyl-2-furfurylamine(66356-53-4)

Safety Data

• Hazard Codes: C
• Statements: 34-36/37/38
• Safety Statements: 26-36/37/39-45
• RIDADR: 2735
• Hazardous Substances Data: 66356-53-4(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 66356-53-4 differently. You can refer to the following data:
1. 2-[[5-(Dimethylaminomethyl)-2-furanyl]methylthio]ethylamine (Ranitidine EP Impurity B) is an impurity of Ranitidine (R120000).
2. 2-[[5-(Dimethylaminomethyl)-2-furanyl]methylthio]ethylamine is an impurity of Ranitidine (R120000).

InChI:InChI=1/C10H18N2OS/c1-12(2)7-9-3-4-10(13-9)8-14-6-5-11/h3-4H,5-8,11H2,1-2H3

Synthetic route

5-[[(2-acetamidoethyl)thio]methyl]-N,N-dimethyl-2-furanmethanamine (79589-16-5) → 5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4)

Conditions	Yield
In water for 2.5h; Reflux; Alkaline conditions;	98%
With water; sodium hydroxide for 2.5h; Reflux;	98%
With sodium hydroxide In water for 2h; Reflux;	94%

(5-dimethylaminomethyl-furan-2-yl)-methanol (15433-79-1) + 2-mercaptoethylamine hydrochloride (156-57-0) → 5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4)

Conditions	Yield
With hydrogenchloride; hydroquinone at 0℃; for 20h;	72%
In hydrogenchloride	56%
In methanol at 120 - 130℃; for 7h;

2-chloroethanamine hydrochloride (870-24-6) + 2-(N,N-dimethylaminomethyl)furyl-5-(methylthiosulfonic) acid (134935-66-3) → 5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In acetonitrile for 5h; Ambient temperature;	65%

2-aminoethylthiosulfonic acid (2937-53-3) + 5-[(dimethylamino)methyl]-furfuryl alcohol hydrochloride (81074-81-9) → 5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4)

Conditions	Yield
With hydrogenchloride 1.) from 50 to 60 deg C, 2 h, 2.) RT, 16 h; Yield given. Multistep reaction;

ranitidine hydrochloride (66357-35-5, 66357-59-3, 71130-06-8) → N-methylnitroacetamide (72078-82-1) + 5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4) + sodium 1-<2-(5-dimethylaminomethylfurfurylthio)ethylamino>-2-nitroethenoxide + methylamine (74-89-5)

Conditions	Yield
With sodium hydroxide In water for 4h; Heating;	A 270 mg B 400 mg C 840 mg D 100 mg
With sodium hydroxide In water for 4h; Mechanism; Product distribution; Ambient temperature; Heating; pH > 9;	A 270 mg B 400 mg C 840 mg D 100 mg

(2-furyl)methyl alcohol (98-00-0) → 5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 70 percent / ethanol / 10 h / Heating 2: 72 percent / conc. HCl, hydroquinone / 20 h / 0 °C View Scheme
Multi-step reaction with 2 steps 1: methanol / 12 h / 70 - 80 °C 2: methanol / 7 h / 120 - 130 °C View Scheme
Multi-step reaction with 2 steps 1: 2.5 h / 90 °C 2: hydrogenchloride / 12 h / 0 - 20 °C View Scheme

5-[(dimethylamino)methyl]-furfuryl alcohol hydrochloride (81074-81-9) → 5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 91.5 percent / aq. sodium thiosulfate, NaOH / 1 h / 30 °C 2: 65 percent / 50percent aq. NaOH / triethylbenzylammonium chloride / acetonitrile / 5 h / Ambient temperature View Scheme

5-chloromethylfurfural (1623-88-7) → 5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: methanol / 1 h / 20 °C 2.2: 0.58 h / 0 - 20 °C 3.1: sodium hydroxide / water / 2 h / Reflux View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: methanol / 0.67 h / 20 °C 2.2: 0.33 h / 0 °C 3.1: water / 2.5 h / Reflux; Alkaline conditions View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / Schlenk technique; Inert atmosphere 1.2: 20 °C / Schlenk technique; Inert atmosphere 2.1: methanol / 0.67 h / 20 °C / Inert atmosphere 2.2: 0.33 h / 0 °C / Inert atmosphere 3.1: sodium hydroxide; water / 2.5 h / Reflux View Scheme

5-[[(2-acetamidoethyl)thio]methyl]furfural (1350914-20-3) → 5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: methanol / 1 h / 20 °C 1.2: 0.58 h / 0 - 20 °C 2.1: sodium hydroxide / water / 2 h / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: methanol / 0.67 h / 20 °C 1.2: 0.33 h / 0 °C 2.1: water / 2.5 h / Reflux; Alkaline conditions View Scheme
Multi-step reaction with 2 steps 1.1: methanol / 0.67 h / 20 °C / Inert atmosphere 1.2: 0.33 h / 0 °C / Inert atmosphere 2.1: sodium hydroxide; water / 2.5 h / Reflux View Scheme

5-hydroxymethyl-2-furfuraldehyde (67-47-0) → 5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: hydrogenchloride / dichloromethane / 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.5 h / Inert atmosphere 2.2: 20 °C / Inert atmosphere 3.1: methanol / 0.67 h / 20 °C 3.2: 0.33 h / 0 °C 4.1: water / 2.5 h / Reflux; Alkaline conditions View Scheme
Multi-step reaction with 4 steps 1.1: hydrogenchloride / dichloromethane; water / 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.5 h / Schlenk technique; Inert atmosphere 2.2: 20 °C / Schlenk technique; Inert atmosphere 3.1: methanol / 0.67 h / 20 °C / Inert atmosphere 3.2: 0.33 h / 0 °C / Inert atmosphere 4.1: sodium hydroxide; water / 2.5 h / Reflux View Scheme

D-fructose (470-23-5, 470-24-6, 10247-46-8, 10489-79-9, 35673-97-3, 36441-90-4, 36441-92-6, 36468-68-5, 37500-17-7, 40461-86-7, 40461-87-8, 41579-20-8, 41846-98-4, 41846-99-5, 41847-00-1, 41847-01-2, 41847-02-3, 41847-03-4, 41847-04-5, 41847-05-6, 41847-06-7, 41847-51-2, 41847-52-3, 42744-42-3) → 5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 1-butyl-3-methylimidazolium chloride; sulfuric acid / 60 °C 2.1: hydrogenchloride / dichloromethane / 20 °C 3.1: sodium hydride / tetrahydrofuran / 0.5 h / Inert atmosphere 3.2: 20 °C / Inert atmosphere 4.1: methanol / 0.67 h / 20 °C 4.2: 0.33 h / 0 °C 5.1: water / 2.5 h / Reflux; Alkaline conditions View Scheme

(5-dimethylaminomethyl-furan-2-yl)-methanol (15433-79-1) + Cysteamine (60-23-1) → 5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4)

Conditions	Yield
With hydrogenchloride at 0 - 20℃; for 12h;

5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4) + p-toluenesulfonyl chloride (98-59-9) → N-(2-(((5-((dimethylamino)methyl)furan-2-yl)methyl)thio)ethyl)-4-methylbenzenesulfonamide

Conditions	Yield
With triethylamine In 1,2-dichloro-ethane at 20℃; for 3h; Inert atmosphere;	98%
With pyridine In dichloromethane at 0℃; for 3h;	10.9%

5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4) + 3-(methylthio)thieno<3,4-d>isothiazole 1,1-dioxide (94662-49-4) → N-[2-[[[5-[(Dimethylamino)methyl]-2-furanyl]methyl]-thio]ethyl]thieno[3,4-d]isothiazol-3-amine 1,1-dioxide (94662-50-7)

Conditions	Yield
In ethanol for 2h; Heating;	96%

di-tert-butyl dicarbonate (24424-99-5) + 5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4) → tert-butyl (2-(((5-((dimethylamino)methyl)furan-2-yl)methyl)thio)ethyl)carbamate (201056-43-1)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 5h; Inert atmosphere;	95%
With dmap; triethylamine In dichloromethane for 12h; Ambient temperature;	50%

5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4) + (1-adamantyl)methyl isocyanate (69887-12-3) → 1-((adamantan-1-yl)methyl)-3-(2-(((5-((dimethylamino)methyl)furan-2-yl)methyl)thio)ethyl)urea

Conditions	Yield
In 1,2-dichloro-ethane at 50℃; for 5h; Inert atmosphere;	94%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4) → Ranitidine (66357-35-5)

Conditions	Yield
In water at 55℃;	92%

5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4) + phenyl isocyanate (103-71-9) → 1-(2-(((5-((dimethylamino)methyl)furan-2-yl)methyl)thio)ethyl)-3-phenylurea

Conditions	Yield
In 1,2-dichloro-ethane at 50℃; for 5h; Inert atmosphere;	91%

1,5-difluoro-2,4-dinitrobenzene (327-92-4) + 5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4) → N-<2-<<<5-<(dimethylamino)methyl>-2-furanyl>methyl>thio>ethyl>-2,4-dinitro-5-fluoroaniline (142744-14-7)

Conditions	Yield
With sodium carbonate In acetonitrile Ambient temperature;	90%

mefenamic Acid (61-68-7) + 5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4) → N-(2-((5-((dimethylamino)methyl)furan-2-yl)methylthio)ethyl)-2-(2,3-dimethylphenylamino)benzamide

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In acetonitrile at 20℃; for 15h;	89%

2-methylamino-2-methylthio-1-nitroethene (102721-76-6, 61832-41-5) + 5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4) → ranitidine (66357-35-5)

Conditions	Yield
In water at 55℃;	88%
In water at 38℃; under 75.0075 - 225.023 Torr; for 7h;
In water at 42℃; for 6h; Time;

3-chloro-1-isocyanatoadamantane + 5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4) → 1-(3-chloroadamantan-1-yl)-3-(2-(((5-((dimethylamino)methyl)furan-2-yl)methyl)thio)ethyl)urea

Conditions	Yield
In 1,2-dichloro-ethane at 50℃; for 5h; Inert atmosphere;	86%

5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4) + 2-Nitrobenzenesulfonyl chloride (1694-92-4) → N-(2-(((5-((dimethylamino)methyl)furan-2-yl)methyl)thio)ethyl)-2-nitrobenzenesulfonamide

Conditions	Yield
With triethylamine In 1,2-dichloro-ethane at 20℃; for 3h; Inert atmosphere;	85%

5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4) + 2,4-Dinitrofluorobenzene (70-34-8) → [2-(5-Dimethylaminomethyl-furan-2-ylmethylsulfanyl)-ethyl]-(2,4-dinitro-phenyl)-amine (142744-13-6)

Conditions	Yield
With sodium carbonate In acetonitrile Ambient temperature;	84%

2-chloro-4-isocyanato-1-methylbenzene (28479-22-3) + 5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4) → 1-(3-chloro-4-methylphenyl)-3-(2-(((5-((dimethylamino)methyl)furan-2-yl)methyl)thio)ethyl)urea (564475-13-4)

Conditions	Yield
In 1,2-dichloro-ethane at 50℃; Inert atmosphere;	81%

1,5-difluoro-2,4-dinitrobenzene (327-92-4) + 5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4) → N,N'-Bis-[2-(5-dimethylaminomethyl-furan-2-ylmethylsulfanyl)-ethyl]-4,6-dinitro-benzene-1,3-diamine (138878-42-9)

Conditions	Yield
With sodium carbonate In acetonitrile for 3h; Heating;	76%

1,1-bis(benzylmercapto)-2-nitroethene (19419-97-7) + 5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4) → (1-benzylsulfanyl-2-nitro-vinyl)-(2-(5-dimethylaminomethyl-furan-2-ylmethylsulfanyl)-ethyl)-amine (136483-96-0)

Conditions	Yield
In toluene at 100℃; for 3h;	75%

phthalic anhydride (85-44-9) + 5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4) → 2-(2-((5-((dimethylamino)methyl)furan-2-yl)methylthio)ethyl)isoindoline-1,3-dione (66356-70-5)

Conditions	Yield
In toluene for 2h; Reflux; Dean-Stark;	72%

1,8-Naphthalic anhydride (81-84-5) + 5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4) → 2-(2-((5-((dimethylamino)methyl)furan-2-yl)methylthio)ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

Conditions	Yield
In toluene for 3h; Reflux; Dean-Stark;	71.1%

5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4) + 1,1-di(methylsulfanyl)-2-nitroethylene (13623-94-4) → 1-<2-<(5-Dimethylaminomethyl-2-furyl)-methylthio>-ethylamino>-1-methylthio-2-nitroethylen (72115-14-1)

Conditions	Yield
In acetonitrile for 10h; Heating;	69%
In acetonitrile Heating;
In acetonitrile for 4h; Heating;
In acetonitrile at 90℃; for 8h;

5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4) + 6-Chloro-1H-benzoimidazole-2-sulfonic acid (40828-56-6) → (6-Chloro-1H-benzoimidazol-2-yl)-[2-(5-dimethylaminomethyl-furan-2-ylmethylsulfanyl)-ethyl]-amine (106135-23-3)

Conditions	Yield
at 130℃; for 1.16667h;	69%

5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4) + 1,1-dioxo-1H-1λ6-[1,2,5]thiadiazole-3,4-diamine (55904-35-3) → 4-<2-<5-(dimethylaminomethyl)furfurylthio>ethylamino>-2,3-dihydro-3-oxo-1,2,5-thiadiazole 1,1-dioxide (78441-44-8) + 3,4-bis<2-<5-(dimethylaminomethyl)furfurylthio>ethylamino>-1,2,5-thiadiazole 1,1-dioxide (78441-31-3)

Conditions	Yield
With ammonium hydroxide for 12h; Ambient temperature;	A 69% B 70 mg

1,4-difluoro-2-nitrobenzene (364-74-9) + 5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4) → [2-(5-Dimethylaminomethyl-furan-2-ylmethylsulfanyl)-ethyl]-(4-fluoro-2-nitro-phenyl)-amine (142744-16-9)

Conditions	Yield
With sodium carbonate In acetonitrile Ambient temperature;	68%

5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4) + 4-amino-2-phenethyl-2,3-dihydro-3-oxo-1,2,5-thiadiazole 1,1-dioxide (106350-11-2) → 4-[2-(5-Dimethylaminomethyl-furan-2-ylmethylsulfanyl)-ethylamino]-1,1-dioxo-2-phenethyl-1,2-dihydro-1λ6-[1,2,5]thiadiazol-3-one (131844-01-4) + C20H29N5O4S2 (131844-03-6)

Conditions	Yield
In ethanol for 18h; Ambient temperature;	A 67% B 13%

5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4) + 1,1-dioxo-1H-1λ6-[1,2,5]thiadiazole-3,4-diamine (55904-35-3) → 3,4-bis<2-<5-(dimethylaminomethyl)furfurylthio>ethylamino>-1,2,5-thiadiazole 1,1-dioxide (78441-31-3)

Conditions	Yield
In water for 12h; Ambient temperature;	67%

5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4) + 4-amino-2-benzyl-2,3-dihydro-3-oxo-1,2,5-thiadiazole 1,1-dioxide (106350-10-1) → 2-benzyl-4-<2-<5-(dimethylaminomethyl)furfurylthio>-ethylamino>-2,3-dihydro-3-oxo-1,2,5-thiadiazole 1,1,-dioxide (131844-00-3) + 2-amino-2-<(N-benzylsulphamoyl)imino>-N-<2-<5-(dimethylaminomethyl)furfurylthio>-ethyl>acetamide (112391-90-9)

Conditions	Yield
In ethanol for 18h; Ambient temperature;	A 66% B 24%
In ethanol Ambient temperature; Yield given;

5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4) + 6-Methyl-1H-benzoimidazole-2-sulfonic acid (106135-27-7) → [2-(5-Dimethylaminomethyl-furan-2-ylmethylsulfanyl)-ethyl]-(6-methyl-1H-benzoimidazol-2-yl)-amine (106135-21-1)

Conditions	Yield
at 130℃; for 1.16667h;	64%

succinic acid anhydride (108-30-5) + 5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4) → 1-(2-((5-((dimethylamino)methyl)furan-2-yl)methylthio)ethyl)pyrrolidine-2,5-dione

Conditions	Yield
With dmap In toluene for 3h; Reflux; Dean-Stark;	63.6%

5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4) + 2-methylsuccinic anhydride (4100-80-5) → 1-(2-((5-((dimethylamino)methyl)furan-2-yl)methylthio)ethyl)-3-methylpyrrolidine-2,5-dione

Conditions	Yield
With dmap In toluene for 2h; Reflux; Dean-Stark;	63.6%

Upstream product

• 15433-79-1 (5-dimethylaminomethyl-furan-2-yl)-methanol 
• 156-57-0 2-mercaptoethylamine hydrochloride 
• 60-23-1 Cysteamine 
• 67-47-0 5-hydroxymethyl-2-furfuraldehyde 
• 79589-16-5 5-[[(2-acetamidoethyl)thio]methyl]-N,N-dimethyl-2-furanmethanamine 
• 1350914-20-3 5-[[(2-acetamidoethyl)thio]methyl]furfural 
• 1623-88-7 5-chloromethylfurfural 
• 81074-81-9 5-[(dimethylamino)methyl]-furfuryl alcohol hydrochloride 
• 98-00-0 (2-furyl)methyl alcohol 
• 66357-35-5 ranitidine hydrochloride 
• 870-24-6 2-chloroethanamine hydrochloride 
• 134935-66-3 2-(N,N-dimethylaminomethyl)furyl-5-(methylthiosulfonic) acid 
• 2937-53-3 2-aminoethylthiosulfonic acid 

Downstream Products

• 138878-42-9 N,N'-Bis-[2-(5-dimethylaminomethyl-furan-2-ylmethylsulfanyl)-ethyl]-4,6-dinitro-benzene-1,3-diamine 
• 142744-14-7 N-<2-<<<5-<(dimethylamino)methyl>-2-furanyl>methyl>thio>ethyl>-2,4-dinitro-5-fluoroaniline 
• 78441-83-5 3-{2-[(5-dimethylaminomethyl-furan-2-yl)methylthio]ethylamino}-4-amino-1,2,5-thiadiazole 1,1-dioxide 
• 136483-96-0 (1-benzylsulfanyl-2-nitro-vinyl)-(2-(5-dimethylaminomethyl-furan-2-ylmethylsulfanyl)-ethyl)-amine 
• 66357-35-5 Ranitidine 
• 66357-35-5 ranitidine 
• 66356-70-5 2-(2-((5-((dimethylamino)methyl)furan-2-yl)methylthio)ethyl)isoindoline-1,3-dione 
• 66357-59-3 ranitidine hydrochloride 
• 564475-13-4 1-(3-chloro-4-methylphenyl)-3-(2-(((5-((dimethylamino)methyl)furan-2-yl)methyl)thio)ethyl)urea 
• 149867-80-1 N-cyano-N'-[3-[N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methylamino]propyl]-N''-[2-[[5-(dimethylaminomethyl)furfuryl]thio]ethyl]guanidine 

Relevant articles and documents

Synthesis of ranitidine (Zantac) from cellulose-derived 5-(chloromethyl)furfural

The biomass-derived platform chemical 5-(chloromethyl)furfural is converted into the blockbuster antiulcer drug ranitidine (Zantac) in four steps with an overall 68% isolated yield. The Royal Society of Chemistry.

Critical Influence of 5-Hydroxymethylfurfural Aging and Decomposition on the Utility of Biomass Conversion in Organic Synthesis

Spectral studies revealed the presence of a specific arrangement of 5-hydroxymethylfurfural (5-HMF) molecules in solution as a result of a hydrogen–bonding network, and this arrangement readily facilitates the aging of 5-HMF. Deterioration of the quality of this platform chemical limits its practical applications, especially in synthesis/pharma areas. The model drug Ranitidine (Zantac) was synthesized with only 15 % yield starting from 5-HMF which was isolated and stored as an oil after a biomass conversion process. In contrast, a much higher yield of 65 % was obtained by using 5-HMF isolated in crystalline state from an optimized biomass conversion process. The molecular mechanisms responsible for 5-HMF decomposition in solution were established by NMR and ESI-MS studies. A highly selective synthesis of a 5-HMF derivative from glucose was achieved using a protecting group at O(6) position.

Synthesis of highly fluorescent and water soluble perylene bisimide

Designed and synthesized a new highly water soluble N,N′-bis(2-((5- ((dimethylamino)methyl)furan-2-yl)methylthio)ethyl)perylene-3,4,9, 10-tetracarboxylic diimide from 2-((5-((dimethylamino)methyl)furan-2-yl) methylthio)ethanamine and perylene-3,4,9,10-tetracarboxylic dianhydride. The compound was characterized by 1H, 13C, 2D NMR, mass and IR techniques. The compound is highly fluorescent with good solubility in water and other polar solvents.