N,N-Diethyl-1,3-benzodioxole-5-carboxamide

Base Information

• Chemical Name: N,N-Diethyl-1,3-benzodioxole-5-carboxamide
• CAS No.: 15777-86-3
• Molecular Formula: C12H15 N O3
• Molecular Weight: 221.2524
• NSC Number: 6030
• UNII: WZ05RJA28U
• DSSTox Substance ID: DTXSID80166315
• Nikkaji Number: J1.905.119F
• Wikidata: Q83035517
• Mol file: 15777-86-3.mol

Synonyms:N,N-Diethyl-1,3-benzodioxole-5-carboxamide;15777-86-3;N,N-Diethyl-3,4-methylenedioxybenzamide;1,3-BENZODIOXOLE-5-CARBOXAMIDE, N,N-DIETHYL-;NSC 6030;N,N-Diethylpiperonylamide;BRN 0204796;WZ05RJA28U;Piperonylamide, N,N-diethyl-;AI3-00813;NSC-6030;4-19-00-03497 (Beilstein Handbook Reference);NSC6030;UNII-WZ05RJA28U;TimTec1_007923;SCHEMBL9488344;DTXSID80166315;HMS1556I03;STL260182;AKOS000677830;IDI1_033577;LS-34648;AB00100093-01

Chemical Property of N,N-Diethyl-1,3-benzodioxole-5-carboxamide

Chemical Property:

• Vapor Pressure: 8.5E-06mmHg at 25°C
• Boiling Point: 374.2°Cat760mmHg
• Flash Point: 180.1°C
• Density: 1.171g/cm³
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 221.10519334
• Heavy Atom Count: 16
• Complexity: 253

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)C(=O)C1=CC2=C(C=C1)OCO2

Technology Process of N,N-Diethyl-1,3-benzodioxole-5-carboxamide

There total 9 articles about N,N-Diethyl-1,3-benzodioxole-5-carboxamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

Piperonylic acid (94-53-1) + diethylamine (109-89-7) → N,N-diethylbenzo[d][1,3]dioxole-5-carboxamide (15777-86-3)

Guidance literature:

With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 5h;

DOI:10.1039/c9ob00699k

Reference yield: 71.0%

benzo[1,3]dioxol-5-yl-diethylamino-acetonitrile (37673-00-0) → N,N-diethylbenzo[d][1,3]dioxole-5-carboxamide (15777-86-3)

Guidance literature:

With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; oxygen; In dimethyl sulfoxide; for 3h;

DOI:10.1055/s-1983-30237

Reference yield: 58.0%

piperonal (120-57-0,30024-74-9) + diethylamine (109-89-7) → N,N-diethylbenzo[d][1,3]dioxole-5-carboxamide (15777-86-3)

Guidance literature:

With sodium cyanide; manganese(IV) oxide; at 18 ℃; for 48h;

DOI:10.1016/j.tet.2008.01.113

upstream raw materials:

3,4-(methylenedioxy)benzoyl chloride

diethylamine

benzo[1,3]dioxol-5-yl-diethylamino-acetonitrile

Piperonylic acid

Downstream raw materials:

7-Phenylsulfanyl-naphtho[1,2-d][1,3]dioxole-6,9-dione

N,N-diethyl-6-(4-methoxybenzoyl)benzo-[1,3]-dioxole-5-carboxamide

(2R,3S,4S,4aR,11bS)-5-Benzyl-2,3,4-tris-benzyloxy-3,4,4a,11b-tetrahydro-2H,5H-[1,3]dioxolo[4,5-j]phenanthridine-1,6-dione

(1S,2S,3S,4S,4aR,11bS)-5-Benzyl-2,3,4-tris-benzyloxy-1-hydroxy-1,3,4,4a,5,11b-hexahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-one

Refernces

• 1、 Wang, Shi-Meng,Zhao, Chuang,Zhang, Xu,Qin, Hua-Li. "Clickable coupling of carboxylic acids and amines at room temperature mediated by SO2F2: A significant breakthrough for the construction of amides and peptide linkages". . p. 4087 - 4101. Retrieved 2019/04/30.
• 2、 Dam, Johan Hygum,Madsen, Robert. "Convergent synthesis of pancratistatin from piperonal and xylose". experimental part. p. 4666 - 4673. Retrieved 2009/12/05.