Benzene → HCID 13913347, compound

HRID 579861Notes

Reaction equation

HRID 579861 reaction equation
C1C=CC=CC=1.[Cl:7][C:8]1[CH:9]=[C:10]([CH:12]=[CH:13][C:14]=1[CH:15]([CH3:17])[CH3:16])[NH2:11].[CH3:18][C:19]1([C:22](Cl)=[O:23])[CH2:21][CH2:20]1>C(N(CC)CC)C>[Cl:7][C:8]1[CH:9]=[C:10]([NH:11][C:22]([C:19]2([CH3:18])[CH2:21][CH2:20]2)=[O:23])[CH:12]=[CH:13][C:14]=1[CH:15]([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 241BenzeneHCID 127899391-Methylcyclopropane-1-carbonyl chlorideHCID 139133463-Chloro-4-isopropylaniline

Product 1

HCID 13913347HCID 13913347, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 90 ml of benzene were added 1.0 g (5.9/1000 mole) of 3-chloro-4-isopropylaniline, 0.7 g of triethylamine, and 0.8 g (6.8/1000 mole) of 1-methylcyclopropanecarboxylic acid chloride. The mixture was stirred for 1 hour at 5° to 10° C. The precipitated crystals were separated by filtration, and the filtrate was washed with a saturated aqueous solution of sodium hydrogen carbonate and dried over anhydrous sodium sulfate. The resulting dried filtrate was concentrated by an evaporator. The resulting oily product was isolated and purified by silica gel column chromatography [eluent: benzene/ethyl acetate=40/1 (v/v)] to give 1.3 g of N-(3-chloro-4-isopropylphenyl)-1-methylcyclopropanecarboxamide as an oil in a yield of 87.6 % based on 3-chloro-4-isopropylaniline. On standing for a long period of time, the oil crystallized.

Workup

  1. customThe precipitated crystals were separated by filtration
  2. washthe filtrate was washed with a saturated aqueous solution of sodium hydrogen carbonate
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe resulting dried filtrate was concentrated by an evaporator
  5. customThe resulting oily product was isolated
  6. custompurified by silica gel column chromatography [eluent: benzene/ethyl acetate=40/1 (v/v)]

Sources & evidence

ORD record
ord-5fb8b2e0d51643f8b9821845de7964da
Source dataset
uspto-grants-1988_06
Patent number
US04749812

Reaction notes

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