Benzoyl chloride, 3,4-dichloro- → HCID 54154087, compound

HRID 1283529Notes

Reaction equation

HRID 1283529 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5](Cl)=[O:6].[NH2:12][CH2:13][C:14]1([N:20]([CH3:28])[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([NH:12][CH2:13][C:14]1([N:20]([CH3:28])[CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:6]

Participants

4

Reactant 2

HCID 76403Benzoyl chloride, 3,4-dichloro-HCID 21409889HCID 21409889, compound

Product 1

HCID 54154087HCID 54154087, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 3,4-dichlorobenzoyl chloride (2.095 g.) in benzene (50 ml) was added to a solution of 1-aminomethyl-N-methyl-N-benzylcyclohexylamine (2.32 g.) in benzene (50 ml) and the mixture heated under reflux for 1 hr. The solution was allowed to cool, washed with 2N sodium hydroxide solution (3 × 50 ml), water (4 × 100 ml), dried (Na2SO4) and evaporated to give a white crystalline solid (4.0 g). Recrystallization from cyclohexane afforded 1-[3,4-dichlorobenzoylaminomethyl]-N-methyl-N-benzylcyclohexylamine (110/39) as white prisms (3.589 g. 89%) m.p. 139°-145°.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 1 hr
  3. temperatureto cool
  4. washwashed with 2N sodium hydroxide solution (3 × 50 ml), water (4 × 100 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-8b1c46447bab4e8cb82262e72581e105
Source dataset
uspto-grants-1976_08
Patent number
US03975443

Reaction notes

Loading…