Benzoyl chloride → 2-Methylcyclohexyl 2-chloro-5-(benzoylamino)benzoate

HRID 1292597Notes

Reaction equation

HRID 1292597 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C:11]1[CH:12]=[CH:13][C:14]([Cl:27])=[C:15]([CH:26]=1)[C:16]([O:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]1[CH3:25])=[O:17].C(N(CC)CC)C>C(Cl)Cl>[Cl:27][C:14]1[CH:13]=[CH:12][C:11]([NH:10][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:26][C:15]=1[C:16]([O:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]1[CH3:25])=[O:17]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 189158082-Methylcyclohexyl 5-amino-2-chlorobenzoate

Product 1

HCID 189158072-Methylcyclohexyl 2-chloro-5-(benzoylamino)benzoateYield 36.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzoyl chloride (5.2 g, 0.037 mole) was added slowly at room temperature to a stirred mixture of 2-methylcyclohexyl 5-amino-2-chlorobenzoate (10 g, 0.037 mole), triethylamine (4.0 g, 0.04 mole) dissolved in methylene chloride (100 ml). This reaction mixture was stirred at room temperature for 20 hours. The reaction mixture was then washed with water (200 ml), 3% HCl solution (100 ml), 2% NaOH solution (100 ml) and water (100 ml), dried (magnesium sulfate) and filtered. The solvent was evaporated off to give a brown oil which was crystallized with ethyl/hexane to give 2-methylcyclohexyl 2-chloro-5-(benzoylamino)benzoate as a white solid (5 g, m.p. 121°-122° C.)

Workup

  1. washThe reaction mixture was then washed with water (200 ml), 3% HCl solution (100 ml), 2% NaOH solution (100 ml) and water (100 ml)
  2. dry with materialdried (magnesium sulfate)
  3. filtrationfiltered
  4. customThe solvent was evaporated off
  5. customto give a brown oil which
  6. customwas crystallized with ethyl/hexane

Sources & evidence

ORD record
ord-4da2801fd58446a4912b2eab47fe0fef
Source dataset
uspto-grants-1998_05
Patent number
US05756813

Reaction notes

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