Triethylamine → HCID 17912566, compound

HRID 963548Notes

Reaction equation

HRID 963548 reaction equation
[F:1][C:2]([F:10])=[CH:3][CH2:4][CH2:5][CH2:6][C:7](Cl)=[O:8].[C:11]1([S:17][C:18]2[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>O1CCCC1>[C:11]1([S:17][C:18]2[CH:24]=[CH:23][C:21]([NH:22][C:7](=[O:8])[CH2:6][CH2:5][CH2:4][CH:3]=[C:2]([F:10])[F:1])=[CH:20][CH:19]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 96081Aniline, p-(phenylthio)- (6CI,7CI,8CI)HCID 197938396,6-Difluorohex-5-enoic acid chloride

Product 1

HCID 17912566HCID 17912566, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

With cooling at 10°, 8.5 g of 6,6-difluorohex-5-enoic acid chloride are added to 10.0 g of 4-phenylthioaniline, 6.5 g of triethylamine and 100 mg of 4-N-pyrrolidinopyridine in 250 ml of tetrahydrofuran. The mixture is stirred for 2 hours at room temperature and then concentrated by evaporation in vacuo. The residue is taken up in toluene, the toluene phase is washed with water, dried over sodium sulfate and 90-95% of the amount of toluene is evaporated off in vacuo. While the mixture is still warm, a small amount of hexane is added, which causes the product to crystallise out. The mixture is cooled and filtered, and the filter residue is washed with hexane, yielding the title compound having a melting point of 80°-81° (compound no. 2-1).

Workup

  1. temperatureWith cooling at 10°
  2. concentrationconcentrated by evaporation in vacuo
  3. washthe toluene phase is washed with water
  4. dry with materialdried over sodium sulfate and 90-95% of the amount of toluene
  5. customis evaporated off in vacuo
  6. temperatureWhile the mixture is still warm
  7. additiona small amount of hexane is added
  8. customto crystallise out
  9. temperatureThe mixture is cooled
  10. filtrationfiltered
  11. washthe filter residue is washed with hexane

Sources & evidence

ORD record
ord-d2e326c8467a4ca5a0fce8241d4f8254
Source dataset
uspto-grants-1998_06
Patent number
US05763481

Reaction notes

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