Dimethylamine → Acetamide

HRID 1659129Notes

Reaction equation

HRID 1659129 reaction equation
Cl.CO[CH:4]([C:8]1C=CC=C[N:9]=1)C(Cl)=O.[CH3:14][O:15][CH:16]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)[C:17](O)=[O:18].S(Cl)(Cl)=O.[CH3:30][NH:31][CH3:32].[OH-].[Na+]>C1C=CC=CC=1.C(Cl)(Cl)Cl>[C:8]([NH2:9])(=[O:15])[CH3:4].[CH3:14][O:15][CH:16]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)[C:17]([N:31]([CH3:32])[CH3:30])=[O:18]

Participants

9

Reactant 5

HCID 674DimethylamineHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 214869142-Methoxy-2-(2-pyridyl)acetyl chloride hydrochlorideHCID 21905598(RS)-Methoxy-pyridin-2-yl-acetic acid

Product 2

HCID 178AcetamideHCID 21486904HCID 21486904, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6212ChloroformSolvent2×

Procedure

Alternatively, 2-methoxy-N,N-dimethyl-2-pyridyl)acetamide is prepared by the following procedure. 2-Methoxy-2-(2-pyridyl)acetyl chloride hydrochloride, 22 g., [prepared by reacting 2-methoxy-2-(2-pyridyl)acetic acid in benzene with thionyl chloride] in 100 ml. of chloroform is added dropwise and with cooling to 50 g. of dimethylamine in 100 ml. of chloroform. The mixture is stirred for 4 hours, then 50 ml. of 5% aqueous sodium hydroxide is added and the chloroform solution is dried and concentrated to give 2-methoxy-N,N-dimethyl-2-(2-pyridyl)acetamide.

Workup

  1. temperaturewith cooling to 50 g
  2. dry with materialthe chloroform solution is dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e78a8420794d470fa3f7713e19d806ab
Source dataset
uspto-grants-1976_06
Patent number
US03966945

Reaction notes

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