2-Chloro-N,N-dimethylethylamine → HCID 13019471, compound

HRID 2285728Notes

Reaction equation

HRID 2285728 reaction equation
[C:1]([CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)#[N:2].[H-].[Na+].[CH3:16][N:17]([CH2:19][CH2:20]Cl)[CH3:18]>CN(C)C=O>[CH3:16][N:17]([CH2:19][CH2:20][CH:3]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)[C:1]#[N:2])[CH3:18]

Participants

5

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 848548Methyl 4-(cyanomethyl)benzoate

Product 1

HCID 13019471HCID 13019471, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 4-cyanomethylbenzoic acid, methyl ester (28.8 g) in dry dimethylformamide (DMF) (100 ml) was added dropwise to a stirred suspension of sodium hydride (80%, dispersion in oil, 5.4 g) in DMF (50 ml) under nitrogen. The mixture was stirred at 50° for 1 h., then a solution of dimethylaminoethyl chloride (21.3 g) in DMF (50 ml) was added and stirring was continued at 50° for 18 h.

Workup

  1. stirringstirring
  2. waitwas continued at 50° for 18 h.

Sources & evidence

ORD record
ord-631e9326a9f14fbeb9976853f8366a3a
Source dataset
uspto-grants-1982_04
Patent number
US04324792

Reaction notes

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