Dichloromethane → N-Allyl-2,2-dichloro-N-(3-(trifluoromethyl)phenyl)acetamide

HRID 2057355Notes

Reaction equation

HRID 2057355 reaction equation
Cl.[CH2:2]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:7]=1)[CH:3]=[CH2:4].C(Cl)Cl.[Cl:19][CH:20]([Cl:24])[C:21](Cl)=[O:22]>C(N(CC)CC)C>[CH2:2]([N:5]([C:21](=[O:22])[CH:20]([Cl:24])[Cl:19])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:13])([F:14])[F:15])[CH:7]=1)[CH:3]=[CH2:4]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6593Dichloroacetyl chlorideHCID 86737076HCID 86737076, compound

Product 1

HCID 109065N-Allyl-2,2-dichloro-N-(3-(trifluoromethyl)phenyl)acetamide

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Twenty-three and eight tenths grams of N-allyl m-trifluoromethyl aniline hydrochloride was suspended in 200 ml. of methylene chloride, 21 g. of triethylamine was added and the mixture stirred in a water bath at room temperature while 15 g. of dichloroacetyl chloride was added dropwise. After stirring about 30 minutes, after addition was complete, the mixture was washed with dilute ~1% sodium hydroxide, dilute ~1% hydrochloric acid and water, separated and dried over magnesium sulfate and the solvent stripped under vacuum. The product was dissolved in ether and treated with 10 g. of 20% ethereal hydrochloric acid, the precipitate filtered off and the ether stripped under vacuum to give 25 g. of product, nD30 1.4740.

Workup

  1. stirringAfter stirring about 30 minutes
  2. additionafter addition
  3. washthe mixture was washed
  4. additionwith dilute ~1% sodium hydroxide
  5. additiondilute ~1% hydrochloric acid and water
  6. customseparated
  7. dry with materialdried over magnesium sulfate
  8. dissolutionThe product was dissolved in ether
  9. additiontreated with 10 g
  10. filtrationof 20% ethereal hydrochloric acid, the precipitate filtered off
  11. customto give 25 g

Sources & evidence

ORD record
ord-0239e29c2e9c436abf74650e35b1adbc
Source dataset
uspto-grants-1980_07
Patent number
US04210589

Reaction notes

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