62780-89-6

Basic information

• Product Name: 1-(3-Chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one
• Synonyms: 1-(3-Chloropropyl)-2-benzimidazolidinone,ca.90%,balance mainly bromo-derivative;1-(3-Chloropropyl)-2-benzimidazolidinone1-(3-Chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one;1-(3-Chloropropyl)-2-benzimidazolidinone, balance mainly bromo-derivative, ca. 90%;1-(3-Chloropropyl)-2-benziMidazolidinone, balance Mainly broMo-derivative, ca. 90% 50GR;1-(3-Chloropropyl)-1,3-dihydrobenziMidazol-2-one;3-(3-chloropropyl)-1H-benzimidazol-2-one;1-(3-chloropropyl)-1H-benzo[d]imidazol-2(3H)-one;1-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-
• CAS NO: 62780-89-6
• Molecular Formula: C₁₀H₁₁ClN₂O
• Molecular Weight: 210.66
• EINECS: 263-731-6
• Product Categories: Aromatics;Heterocycles;Intermediates
• Mol File: 62780-89-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: 115-125 °C
• Appearance: White to slightly beige/Powder
• Density: 1.2798 (rough estimate)
• Vapor Pressure: 0.017Pa at 25℃
• Refractive Index: 1.5330 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 12.11±0.30(Predicted)
• Water Solubility: 210 mg/L (20 ºC)
• CAS DataBase Reference: 1-(3-Chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-Chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one(62780-89-6)
• EPA Substance Registry System: 1-(3-Chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one(62780-89-6)

Safety Data

• Hazard Codes: Xn,T
• Statements: 22-41-37/38-25
• Safety Statements: 38-28A-45-39-26
• Hazardous Substances Data: 62780-89-6(Hazardous Substances Data)

Usage

Chemical Properties

1-(3-Chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one is WHITE TO SLIGHTLY BEIGE POWDER

Uses

1-(3-Chloropropyl)-1,3-dihydrobenzimidazol-2-one is a benzimidazole derivative used in the preparation of neuroleptic and antiallergic agents.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C10H11ClN2O/c11-6-3-7-13-9-5-2-1-4-8(9)12-10(13)14/h1-2,4-5H,3,6-7H2,(H,12,14)

Synthetic route

1-(3-chloropropyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one (62780-84-1) → 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6)

Conditions	Yield
With phosphoric acid; propiononitrile at 75℃; for 4h; Concentration; Temperature;	92%
With hydrogenchloride In methanol; water at 20℃; Solvent; Reagent/catalyst;	90%
In hydrogenchloride; ethanol	9.5 parts (90%)

1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one (52099-72-6) + 1,3-chlorobromopropane (109-70-6) → 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6)

Conditions	Yield
With sulfuric acid; sodium ethanolate 1) EtOH, reflux 4 h; 2) r.t., 2 h; Yield given. Multistep reaction;

(2-Amino-phenyl)-(3-chloro-propyl)-carbamic acid ethyl ester (100460-85-3) → 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6)

Conditions	Yield
With calcium chloride at 210℃; for 1.5h; Yield given;

1-(3-chloropropyl)2-nitroaniline (62781-00-4) → 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: xylene / 18 h / Heating 2: H2 / 10percent Pd/C / methanol / 4 h 3: CaCl2 / 1.5 h / 210 °C View Scheme

(3-Chloro-propyl)-(2-nitro-phenyl)-carbamic acid ethyl ester (100460-82-0) → 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / 10percent Pd/C / methanol / 4 h 2: CaCl2 / 1.5 h / 210 °C View Scheme

1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) + methyl iodide (74-88-4) → 1-(3-chloropropyl)-1,3-dihydro-3-methyl-2H-benzimidazol-2-one (78056-57-2)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h;	98%
With sodium hydroxide In water; acetonitrile at 20℃; for 18h;	86%

5-ethyl-5H-[1,2,4]triazino[5,6-b]indole-3-thiol (36047-55-9) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-(3-(5-ethyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylthio)propyl)-1H-benzo[d]imidazol-2(3H)-one (433261-68-8)

Conditions	Yield
Stage #1: 5-ethyl-5H-[1,2,4]triazino[5,6-b]indole-3-thiol With potassium hydroxide In water at 20℃; for 2h; Stage #2: 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one In water at 90℃; for 24h;	93.9%

formaldehyd (50-00-0) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-(3-chloropropyl)-3-(hydroxymethyl)-1H-benzo[d]imidazol-2(3H)-one (1352949-10-0)

Conditions	Yield
With sodium acetate; acetic acid at 65℃; for 20h;	90%

1-(6,11-dihydrodibenzothiepin-11-yl)piperazine (121942-88-9) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-(3-(4-(6,11-dihydrodibenzothiepin-11-yl)-1-piperazinyl)propyl)-1,3-dihydro-2H-benzimidazol-2-one (121942-94-7)

Conditions	Yield
With triethylamine; potassium iodide In toluene Heating;	83%

1-(8-chloro-10,11-dihydrodibenzo[b,f]thiepin-10-yl)piperazine (23048-89-7) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-(3-(4-(8-chloro-10,11-dihydrodibenzothiepin-10-yl)-1-piperazinyl)propyl)-1,3-dihydro-2H-benzimidazol-2-one (121943-04-2)

Conditions	Yield
With triethylamine; potassium iodide In toluene Heating;	76%

2-methyl-3-(1,2,3,6-tetrahydro-pyridin-4-yl)-1H-indole (84461-65-4) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-{3-[4-(2-Methyl-1H-indol-3-yl)-3,6-dihydro-2H-pyridin-1-yl]-propyl}-1,3-dihydro-benzoimidazol-2-one (84461-66-5)

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide for 18h; Heating;	76%

1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) + 1-(2-chloro-10,11-dihydro-dibenzo[b,f]thiepin-10-yl)-piperazine (52548-24-0) → 1-(3-(4-(2-chloro-10,11-dihydrodibenzothiepin-10-yl)-1-piperazinyl)propyl)-1,3-dihydro-2H-benzimidazol-2-one (121943-02-0)

Conditions	Yield
With triethylamine; potassium iodide In toluene Heating;	73%

1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) + 3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (65347-55-9) → 1-{3-[4-(1H-Indol-3-yl)-3,6-dihydro-2H-pyridin-1-yl]-propyl}-1,3-dihydro-benzoimidazol-2-one

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide for 18h; Heating;	69%

8-methylthio-10-piperazino-10,11-dihydrodibenzothiepin (27139-61-3) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-(3-(4-(8-(methylthio)-10,11-dihydrodibenzothiepin-10-yl)-1-piperazinyl)propyl)-1,3-dihydro-2H-benzimidazol-2-one (121943-06-4)

Conditions	Yield
With triethylamine; potassium iodide In toluene Heating;	67%

1-(10,11-dihydrodibenzo[b,f]thiepin-10-yl)piperazine (4774-29-2) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-(3-(4-(10,11-dihydrodibenzothiepin-10-yl)-1-piperazinyl)propyl)-1,3-dihydro-2H-benzimidazol-2-one (121943-00-8)

Conditions	Yield
With triethylamine; potassium iodide In toluene Heating;	65%

1-(2-methyl-6,11-dihydrodibenzothiepin-11-yl)piperazine (121942-90-3) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-(3-(4-(2-methyl-6,11-dihydrodibenzothiepin-11-yl)-1-piperazinyl)propyl)-1,3-dihydro-2H-benzimidazol-2-one (121942-96-9)

Conditions	Yield
With triethylamine; potassium iodide In toluene Heating;	65%

diphenylmethylpiperazine (841-77-0) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → oxatomide (60607-34-3)

Conditions	Yield
With triethylamine; potassium iodide In toluene for 20h; Heating;	64%

3-(4-piperidinyl)-1H-indole (17403-09-7) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → N-{3-[4-(3-indolyl)-piperidino]-propyl}-benzimidazolone (97181-10-7)

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide for 28h; Heating;	61%

1-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)piperazine (69159-50-8) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-(3-(4-(10,11-dihydro-5H-dibenzocycloheptene-5-yl)-1-piperazinyl)propyl)-1,3-dihydro-2H-benzimidazol-2-one (121942-92-5)

Conditions	Yield
With triethylamine; potassium iodide In toluene Heating;	60%

4-propyloxypiperidine (88536-11-2) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-(3-(4-Butylpiperidine-1-yl)propyl)-1,3-dihydro-benzimidazol-2-one (509147-41-5)

Conditions	Yield
With potassium carbonate; sodium iodide	60%
With potassium carbonate; sodium iodide	60%

5-allyl-5H-[1,2,4]triazino[5,6-b]indole-3-thiol (247571-59-1) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-(3-(5-allyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylthio)propyl)-1H-benzo[d]imidazol-2(3H)-one (442653-38-5)

Conditions	Yield
Stage #1: 5-allyl-5H-[1,2,4]triazino[5,6-b]indole-3-thiol With potassium hydroxide In water at 20℃; for 2h; Stage #2: 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one In water at 90℃; for 24h;	55.2%

1-(2-ethoxyethyl)-2-(1-piperazinyl)-1H-benzimidazole (87233-69-0) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-<3-<4-<1-(2-ethoxyethyl)-1H-benzimidazol-2-yl>-1-piperazinyl>propyl>-1,3-dihydro-2H-benzimidazol-2-one (127533-18-0)

Conditions	Yield
With potassium carbonate In toluene for 14h; Heating;	53%

1-(4,9-dihydrothieno<2,3-c>-2-benzothiepin-4-yl)piperazine (121942-91-4) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-(3-(4-(4,9-dihydrothieno<2,3-c>-2-benzothiepin-4-yl)-1-piperazinyl)propyl)-1,3-dihydro-2H-benzimidazol-2-one (121942-98-1)

Conditions	Yield
With triethylamine; potassium iodide In toluene Heating;	50%

4-(indolyl-2)-piperidine + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 4-(indolyl-2)-1-benzimidazolonylpropyl-piperidine

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide for 18h; Heating;	49%

5-allyl-8-methyl-5H-[1,2,4]triazino[5,6-b]indole-3-thiol (304003-33-6) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-(3-(5-allyl-8-methyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylthio)propyl)-1H-benzo[d]imidazol-2(3H)-one (1207874-69-8)

Conditions	Yield
Stage #1: 5-allyl-8-methyl-5H-[1,2,4]triazino[5,6-b]indole-3-thiol With potassium hydroxide In water at 20℃; for 2h; Stage #2: 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one In water at 90℃; for 24h;	47.6%

4-ethylpiperidin-4-ol (550369-44-3) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-[3-(4-Ethyl-4-hydroxypiperidin-1-yl)propyl]-1,3-dihydrobenzoimidazol-2-one

Conditions	Yield
With sodium carbonate; sodium iodide In acetonitrile for 4h; Heating / reflux;	43%

6-Methoxy-3-(4-piperidyl)-1,2-benzisoxazole hydrobromide (84163-17-7) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-{3-[4-(6-Methoxy-benzo[d]isoxazol-3-yl)-piperidin-1-yl]-propyl}-1,3-dihydro-benzoimidazol-2-one (84243-01-6)

Conditions	Yield
With sodium carbonate; potassium iodide In various solvent(s) at 117℃; for 16h;	37%

4-(5-fluoro-1,2-benzisoxazol-3-yl)piperidine hydrochloride (84163-16-6) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-{3-[4-(5-Fluoro-benzo[d]isoxazol-3-yl)-piperidin-1-yl]-propyl}-1,3-dihydro-benzoimidazol-2-one (84242-99-9)

Conditions	Yield
With sodium carbonate; potassium iodide In various solvent(s) at 117℃; for 8h;	36%

5,6-dimethoxy-3-(4-piperidyl)-1,2-benzisoxazole hydrobromide (84163-15-5) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-{3-[4-(5,6-Dimethoxy-benzo[d]isoxazol-3-yl)-piperidin-1-yl]-propyl}-1,3-dihydro-benzoimidazol-2-one (84243-16-3)

Conditions	Yield
With sodium carbonate; potassium iodide In various solvent(s) at 117℃; for 6h;	28%

6-fluoro-3-(piperidin-4-yl)benzo[d]isoxazole hydrochloride (84163-13-3) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-{3-[4-(6-Fluoro-benzo[d]isoxazol-3-yl)-piperidin-1-yl]-propyl}-1,3-dihydro-benzoimidazol-2-one (84243-00-5)

Conditions	Yield
With sodium carbonate; potassium iodide In various solvent(s) at 117℃; for 12h;	27%

4-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (95742-20-4) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 4-fluoro-3-<1-<3-(1,3-dihydro-2-oxo-2H-benzimidazol-1-yl)propyl>-4-piperidinyl>-1,2-benzisoxazole (84243-18-5)

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 90℃; for 6h;	26%

5-methoxy-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (66611-26-5) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-{3-[4-(5-Methoxy-1H-indol-3-yl)-3,6-dihydro-2H-pyridin-1-yl]-propyl}-1,3-dihydro-benzoimidazol-2-one (97181-09-4)

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide for 6h; Heating;	25%

3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride (84163-22-4) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-[3-(4-Benzo[d]isoxazol-3-yl-piperidin-1-yl)-propyl]-1,3-dihydro-benzoimidazol-2-one (84231-49-2)

Conditions	Yield
With sodium carbonate; potassium iodide In various solvent(s) at 117℃; for 6h;	23%

4-Butyl-piperidin-4-ol (22093-38-5) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-[3-(4-Butyl-4-hydroxypiperidin-1-yl)propyl]-1,3-dihydrobenzoimidazol-2-one

Conditions	Yield
With sodium carbonate; sodium iodide In acetonitrile for 2h; Heating / reflux;	23%

Upstream product

• 62780-84-1 1-(3-chloropropyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one 
• 100460-82-0 (3-Chloro-propyl)-(2-nitro-phenyl)-carbamic acid ethyl ester 
• 62781-00-4 1-(3-chloropropyl)2-nitroaniline 
• 100460-85-3 (2-Amino-phenyl)-(3-chloro-propyl)-carbamic acid ethyl ester 
• 52099-72-6 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one 
• 109-70-6 1.3-chlorobromopropane 

Downstream Products

• 62781-08-2 8-[3-(2-oxo-2,3-dihydro-benzoimidazol-1-yl)-propyl]-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one 
• 57808-66-9 domperidone 
• 62781-12-8 3-methyl-8-[3-(2-oxo-2,3-dihydro-benzoimidazol-1-yl)-propyl]-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one 
• 359879-00-8 2-(4-methoxyphenyl)-N-(4-methylbenzyl)-N-(1-(3-(1,3-dihydro-2H-benzimidazol-2-one-1-yl)propyl)piperidine-4-yl) acetamide trifluoroacetate 
• 1352949-08-6 tert-butyl 3-((8-(3-(3-(heptanoyloxymethyl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate 
• 65214-93-9 1-[3-{4-[α-(4-fluorophenyl)-α-phenylmethyl]-1-piperazinyl}propyl]-1,3-dihydro-2H-benzimidazol-2-one 
• 62781-13-9 1-(4-chloro-3-methyl-phenyl)-8-[3-(2-oxo-2,3-dihydro-benzoimidazol-1-yl)-propyl]-1,3,8-triaza-spiro[4.5]decan-4-one 
• 62781-57-1 1-{3-[4-(4-chloro-phenyl)-4-hydroxy-piperidin-1-yl]-propyl}-1,3-dihydro-benzoimidazol-2-one 
• 60607-34-3 oxatomide 

Relevant articles and documents

Method for synthesizing 1-(3-chloropropyl)-benzimidazole-2-ketone

The invention provides a method for synthesizing 1-(3-chloropropyl)-benzimidazole-2-ketone. The reaction route is shown in the description. The method has the beneficial effects that 1, the inventiondesigns the novel synthesis route to prepare a domperidone intermediate with the structure shown in the formula (DOM-4), and the novel synthesis route is realized; the reaction selectivity of the route is good, the controllability is strong, and the route is quite favorable for the implementation of large-scale industrial production; 2, by using the route and the method provided by the invention,the production cost of the domperidone intermediate is greatly lowered, and the purity of the domperidone intermediate is increased, so that the production cost of the domperidone intermediate is greatly reduced.

2-SULFANYL-BENZOIMIDAZOL-1-YL-ACETIC ACID DERIVATIVES AS CRTH2 ANTAGONISTS

The invention relates to 2-sulfanyl-benzoimidazol-1-yl-acetic acid derivatives and their use as potent "chemoattractant receptor-homologous molecule expressed on Th2 cells" antagonists in the treatment of prostaglandin mediated diseases, to pharmaceutical compositions containing these derivatives and to processes for their preparation.

A New Approach to 1-Alkyl-1,3-dihydro-2H-benzimidazol-2-ones

A new procedure for preparing 1-alkyl-1,3-dihydro-2H-benzimidazol-2-ones from o-nitroanilines by succesive ethoxycarbonylation, catalytic hydrogenation and thermal cyclization under neutral conditions is described. - (Keywords: Thermal cyclization)