Water → HCID 28386326, compound

HRID 1041636Notes

Reaction equation

HRID 1041636 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)[O:4][C:2]2=O.[CH3:13][NH:14][CH2:15][CH2:16][C:17]#[N:18].O>CN(C)C=O>[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([N:14]([CH2:15][CH2:16][C:17]#[N:18])[CH3:13])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 8359Isatoic AnhydrideHCID 69656Propanenitrile, 3-(methylamino)-

Product 1

HCID 28386326HCID 28386326, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To Isatoic Anhydride (4.60 g, 28.2 mmol) in N,N-Dimethylformamide (30 mL) was added 3-Methylamino-propionitrile (3.00 mL, 32.1 mmol) and the reaction was stirred under an atmosphere of Nitrogen. After 6 h, the mixture was poured into 200 mL water, then extracted 3×100 mL DCM, washed with 100 mL satd. sodium bicarbonate, which was back extracted with 50 mL DCM. The combined organics were washed with brine (100 mL) and dried over sodium sulfate, then conc. in vacuo afforded 2-Amino-N-(2-cyano-ethyl)-N-methyl-benzamide as an oil in quantitative yield. 1H-NMR: 7.18 (dd, 1H, J=9.0, 9.0 Hz), 7.13 (d, 1H, J=7.3 Hz), 6.74 (m, 2H), 4.31 (br s, 2H), 3.76 (t, 2H, J=6.6 Hz), 3.15 (s, 3H), 2.75 (t, 2H, J=6.6 Hz).

Workup

  1. extractionextracted 3×100 mL DCM
  2. washwashed with 100 mL
  3. extractionsodium bicarbonate, which was back extracted with 50 mL DCM
  4. washThe combined organics were washed with brine (100 mL)
  5. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-dfd53dcc928e4a47a20d48fe3e4d4270
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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