Benzoyl chloride, 3,4-dichloro- → HCID 21409887, compound

HRID 1283552Notes

Reaction equation

HRID 1283552 reaction equation
[CH2:1]([CH2:4][NH:5][C:6]([CH3:10])([CH3:9])[CH2:7][NH2:8])[CH:2]=[CH2:3].[Cl:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=1[Cl:21])[C:15](Cl)=[O:16]>C1C=CC=CC=1.C(OCC)(=O)C>[Cl:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=1[Cl:21])[C:15]([NH:8][CH2:7][C:6]([NH:5][CH2:4][CH2:1][CH:2]=[CH2:3])([CH3:10])[CH3:9])=[O:16]

Participants

5

Reactant 2

HCID 76403Benzoyl chloride, 3,4-dichloro-HCID 55284641HCID 55284641, compound

Product 1

HCID 21409887HCID 21409887, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-allylmethylamino-2-methylpropylamine (1.3 g.,) and 3,4-dichlorobenzoyl chloride (3.15 g.,) was heated under reflux in dry benzene (150 ml.) for 1 hrs. The cooled mixture was washed with dilute sodium hydroxide solution (2 × 30 ml.), water (2 × 30 ml.), dried (MgSO4) and the solvent was removed in vacuo to give a yellow oil (3.9 g.). The oil was passed through a column of alumina 40 × 2.5 cm. using ethyl acetate as an eluent to give 3,4-dichloro-N-(2-allylmethylamino-2-methylpropyl)-benzamide as a pale yellow liquid (2.25 g., 71%).

Workup

  1. temperaturewas heated
  2. washThe cooled mixture was washed with dilute sodium hydroxide solution (2 × 30 ml.), water (2 × 30 ml.)
  3. dry with materialdried (MgSO4)
  4. customthe solvent was removed in vacuo
  5. customto give a yellow oil (3.9 g.)

Sources & evidence

ORD record
ord-c1aed0066f4d4542833561533574a618
Source dataset
uspto-grants-1976_08
Patent number
US03975443

Reaction notes

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