3-(Trifluoromethyl)aniline → HCID 21414098, compound

HRID 442294Notes

Reaction equation

HRID 442294 reaction equation
[CH3:1][N:2]([S:6]([CH3:9])(=[O:8])=[O:7])[C:3](Cl)=[O:4].C(N(CC)CC)C.[F:17][C:18]([F:27])([F:26])[C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=1)[NH2:22]>O1CCCC1>[CH3:1][N:2]([S:6]([CH3:9])(=[O:8])=[O:7])[C:3]([NH:22][C:21]1[CH:23]=[CH:24][CH:25]=[C:19]([C:18]([F:17])([F:26])[F:27])[CH:20]=1)=[O:4]

Participants

5

Reactant 3

HCID 73753-(Trifluoromethyl)anilineHCID 8471TriethylamineHCID 21414088HCID 21414088, compound

Product 1

HCID 21414098HCID 21414098, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution OF 11.4 g of N-methyl-N-methylsulfonyl-carbamoyl chloride in 100 ml of tetrahydrofuran was slowly added at 10° C. to a mixture of 60 ml of tetrahydrofuran, 10.1 g of triethylamine and 16.1 g of 3-trifluoromethylaniline, and after stirring for 16 hours, the mixture was filtered. The filtrate was distilled to dryness under reduced pressure. The residue was added to isopropyl ether and the precipitate formed was recovered by vacuum filtration and was washed and dried to obtain 8 g of N-methyl-N-methylsulfonyl-N'-(3-trifluoromethylphenyl)-urea melting at 72° C. The melting point was unchanged after crystallization from isopropyl ether.

Workup

  1. filtrationthe mixture was filtered
  2. distillationThe filtrate was distilled to dryness under reduced pressure
  3. additionThe residue was added to isopropyl ether
  4. customthe precipitate formed
  5. filtrationwas recovered by vacuum filtration
  6. washwas washed
  7. customdried

Sources & evidence

ORD record
ord-48dc46e9165e4e1997de26e53206a081
Source dataset
uspto-grants-1977_08
Patent number
US04045209

Reaction notes

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