Toluene → 2-Chloro-N-(4-fluorophenyl)-N-(1-methylethyl)acetamide

HRID 1649528Notes

Reaction equation

HRID 1649528 reaction equation
C1(C)C=CC=CC=1.[F:8][C:9]1[CH:18]=[CH:17][C:12]([NH:13][CH:14]([CH3:16])[CH3:15])=[CH:11][CH:10]=1.[Cl:19][CH2:20][C:21](Cl)=[O:22]>N1C=CC=CC=1>[Cl:19][CH2:20][C:21]([N:13]([CH:14]([CH3:16])[CH3:15])[C:12]1[CH:17]=[CH:18][C:9]([F:8])=[CH:10][CH:11]=1)=[O:22]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6577Chloroacetyl chlorideHCID 154403Benzenamine, 4-fluoro-N-(1-methylethyl)-

Product 1

HCID 109662942-Chloro-N-(4-fluorophenyl)-N-(1-methylethyl)acetamideYield 97%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 100 ml dry toluene 15.3 g (0.1 m) 4-fluoro-N-isopropylaniline and 8.7 ml (0.11 m) pyridine were added and stirred. To this solution 12.4 g (0.11 m) chloroacetyl chloride was added dropwise below 25° C. It was allowed to stir overnight at room temperature and the mixture was washed with 2×100 ml water. The organic layer was dried on anhydrous magnesium sulfate and evaporated to give 22.2 g pale yellow liquid, yield 97%.

Workup

  1. stirringto stir overnight at room temperature
  2. washthe mixture was washed with 2×100 ml water
  3. dry with materialThe organic layer was dried on anhydrous magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-33bf82556142469ea8d4ad89df99b932
Source dataset
uspto-grants-1983_11
Patent number
US04418021

Reaction notes

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