Acrylonitrile → HCID 13364789, compound

HRID 2231872Notes

Reaction equation

HRID 2231872 reaction equation
[OH-].[CH2:2]([N+:9](C)(C)C)[C:3]1C=CC=C[CH:4]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:28]=[CH:29][C:30]=1[O:31][CH3:32])[C:18]([NH:20][CH2:21][C:22]1[NH:23][C:24]([CH3:27])=[CH:25][CH:26]=1)=[O:19].C(#N)C=C>C(Cl)Cl>[C:2]([CH2:3][CH2:4][N:23]1[C:24]([CH3:27])=[CH:25][CH:26]=[C:22]1[CH2:21][NH:20][C:18](=[O:19])[C:17]1[CH:28]=[CH:29][C:30]([O:31][CH3:32])=[C:15]([O:14][CH3:13])[CH:16]=1)#[N:9]

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 66854Benzyltrimethylammonium hydroxideHCID 13364787HCID 13364787, compound

Product 1

HCID 13364789HCID 13364789, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3 ml of benzyltrimethyl-ammonium hydroxide (40% strength solution in methanol) are added dropwise to 5.1 g (0.019 mol) of 2-(3,4-dimethoxybenzoylamino-methyl)-5-methyl-pyrrole (compare Example 16) and 15 ml (0.23 mol) of acrylonitrile, while cooling. After 30 minutes, methylene chloride is added, the mixture is filtered, water is added, and the methylene chloride phase is separated off and concentrated. Recrystallisation from ethyl acetate gives 4.3 g of product of melting point: 175° to 176° C.

Workup

  1. temperaturewhile cooling
  2. filtrationthe mixture is filtered
  3. additionwater is added
  4. customthe methylene chloride phase is separated off
  5. concentrationconcentrated
  6. customRecrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-ac678fc8f94847be88eedf1e5fa12898
Source dataset
uspto-grants-1988_11
Patent number
US04785010

Reaction notes

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