Cyclohexylamine → 4-Chloro-N-cyclohexylbenzamide

HRID 917941Notes

Reaction equation

HRID 917941 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1>C1C=CC=CC=1>[CH:1]1([NH:7][C:13](=[O:14])[C:12]2[CH:16]=[CH:17][C:9]([Cl:8])=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 85014-Chlorobenzoyl chloride

Product 1

HCID 2254614-Chloro-N-cyclohexylbenzamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Procedure

Cyclohexylamine (80 gm., 0.8 mole) is dissolved in 2.5 l. of benzene and treated dropwise with 70 gm. (0.4 mole) of p-chlorobenzoyl chloride in 250 ml. of benzene over 45 minutes with intermittent cooling to maintain reaction temperature between 22°-30°. After stirring an additional 15 minutes, the mixture is diluted with benzene and washed with water. A suspended solid is filtered and the filtrate concentrated to 1 l. to give a second crop; these are combined and recrystallized from methanol, 65.0 gm. (68.5%), m.p. 191°-193°.

Workup

  1. temperatureto maintain
  2. customreaction temperature between 22°-30°
  3. washwashed with water
  4. filtrationA suspended solid is filtered
  5. concentrationthe filtrate concentrated to 1 l
  6. customto give a second crop
  7. customrecrystallized from methanol, 65.0 gm

Sources & evidence

ORD record
ord-b7a4ae08bdec4dbd8c3a1c537b74182d
Source dataset
uspto-grants-1976_07
Patent number
US03968211

Reaction notes

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