O-Toluidine → HCID 4406746, compound

HRID 1389935Notes

Reaction equation

HRID 1389935 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:8].[Cl:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:11]=1[C:12](Cl)=[O:13]>CN(C)C1C=CN=CC=1.ClC(Cl)Cl>[Cl:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:11]=1[C:12]([NH:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])=[O:13]

Participants

5

Reactant 2

HCID 7242O-ToluidineHCID 783922,6-Dichlorobenzoyl chloride

Product 1

HCID 4406746HCID 4406746, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of 42.8 parts of 2-methylbenzenamine in 375 parts of trichloromethane are added dropwise 41.8 parts of 2,6-dichlorobenzoyl chloride at reflux temperature. Then there are added 1.2 parts of N,N-dimethyl-4-pyridinamine and stirring is continued for 3 hours at reflux. The reaction mixture is allowed to cool to room temperature overnight and diluted with 375 parts of trichloromethane. The organic phase is washed successively with 100 parts of water, 100 parts of a hydrochloric acid solution 3 N and again 100 parts of water, dried, filtered and evaporated. The residue is crystallized from 200 parts of 2-propanol, yielding 40.6 parts (72.5%) 2,6-dichloro-N-(2-methylphenyl)benzamide; mp. 182.5° C.

Workup

  1. temperatureat reflux temperature
  2. temperatureat reflux
  3. washThe organic phase is washed successively with 100 parts of water, 100 parts of a hydrochloric acid solution 3 N and again 100 parts of water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is crystallized from 200 parts of 2-propanol

Sources & evidence

ORD record
ord-ea16cceab6944f98a3d3018234e15f11
Source dataset
uspto-grants-1981_01
Patent number
US04246429

Reaction notes

Loading…