Water → HCID 13314712, compound

HRID 543572Notes

Reaction equation

HRID 543572 reaction equation
[CH3:1][C:2]1([C:5]([OH:7])=O)[CH2:4][CH2:3]1.[Cl:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][C:15]=1[O:16][CH2:17][C:18]([F:21])([F:20])[F:19])[NH2:12].O>N1C=CC=CC=1>[Cl:8][C:9]1[CH:10]=[C:11]([NH:12][C:5]([C:2]2([CH3:1])[CH2:4][CH2:3]2)=[O:7])[CH:13]=[CH:14][C:15]=1[O:16][CH2:17][C:18]([F:20])([F:21])[F:19]

Participants

5

Reactant 3

HCID 962WaterHCID 813261-Methylcyclopropanecarboxylic acidHCID 1330552583190-04-9

Product 1

HCID 13314712HCID 13314712, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of 1-methylcyclopropanecarboxylic acid (1.8 g) in pyridine (50 ml), a solution of 3-chloro-4-(2,2,2-trifluoroethoxy)aniline (2.3 g) in pyridine (10 ml) cooled with ice was dropwise added while stirring. After stirring at room temperature for 10 hours, the reaction mixture was admixed with water and extracted with ether. The extract was washed with 1 N hydrochloric acid, sodium hydrogen carbonate solution and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated. The crude crystals (2.8 g) were recrystallized from ethanol to give N-(3-chloro-4-(2,2,2-trifluoroethoxy)phenyl)-1-methylcyclopropanecarboxamide (2.6 g). M.P., 95°-96° C.

Workup

  1. additionwas dropwise added
  2. stirringAfter stirring at room temperature for 10 hours
  3. extractionextracted with ether
  4. washThe extract was washed with 1 N hydrochloric acid, sodium hydrogen carbonate solution and saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe crude crystals (2.8 g) were recrystallized from ethanol

Sources & evidence

ORD record
ord-87150c4725c24e0a9f9f199c45308877
Source dataset
uspto-grants-1984_05
Patent number
US04447260

Reaction notes

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