Methylamine → Benzamide, 4-chloro-N-methyl-

HRID 2397642Notes

Reaction equation

HRID 2397642 reaction equation
[CH3:1][NH2:2].[Cl:3][C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1>C(Cl)Cl>[Cl:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH:2][CH3:1])=[O:9])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 85014-Chlorobenzoyl chloride

Product 1

HCID 101339Benzamide, 4-chloro-N-methyl-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The starting material is prepared as follows: To a mixture of 1250 ml of a 40% aqueous solution of methylamine and 1250 ml of methylene chloride, cooled in an ice bath, is added with stirring a solution of 500 g of 4-chlorobenzoyl chloride in 625 ml of methylene chloride. After the addition (50 minutes), the mixture is stirred for an additional 2 hours. The white precipitate is filtered off and air dried and the methylene chloride layer of the filtrate is dried and evaporated to give the crude 4-chloro-N-methyl-benzamide, which, after crystallization from 1200 ml of methanol, melts at 158°-161°; an additional amount of the product is recovered from the mother liquor, m.p. 158°-160°.

Workup

  1. customThe starting material is prepared
  2. temperaturecooled in an ice bath
  3. additionis added
  4. additionAfter the addition (50 minutes)
  5. filtrationThe white precipitate is filtered off
  6. customair dried
  7. dry with materialthe methylene chloride layer of the filtrate is dried
  8. customevaporated

Sources & evidence

ORD record
ord-00b6e056b0e543e9878a14b93acd3588
Source dataset
uspto-grants-1977_05
Patent number
US04022800

Reaction notes

Loading…