Hydrochloric Acid → HCID 21712908, compound

HRID 650618Notes

Reaction equation

HRID 650618 reaction equation
[F:1][C:2]([F:9])=[CH:3][CH2:4][CH2:5][S:6](Cl)=[O:7].[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH2:16])=[CH:13][CH:12]=1.O.Cl>C(OCC)C.C(OCC)(=O)C.CCCCCC>[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH:16][S:6]([CH2:5][CH2:4][CH:3]=[C:2]([F:9])[F:1])=[O:7])=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 660364-ChlorobenzylamineHCID 21712905HCID 21712905, compound

Product 1

HCID 21712908HCID 21712908, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

4,4-Difluorobut-3-enyl sulfinylchloride (0.5 g) in dry diethyl ether (1.5 ml) was stirred at ambient temperature and 4-chlorobenzylamine (1.0 g) in diethyl ether (1.5 ml) was added dropwise. The mixture was stored at ambient temperature for 2 days then water (100 ml) added. The mixture was made acidic with aqueous hydrochloric acid (2M) and extracted with dichloromethane (100 ml). The organic fraction was separated, washed with water then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give an oil which was fractionated by chromatography (silica; ethyl acetate/hexane 2:1 by volume) to give N-4-chlorobenzyl 4,4-difluorobut-3-enyl-sulfinamide, 0.094 g, as an off-white solid, mp37-8° C.

Workup

  1. extractionextracted with dichloromethane (100 ml)
  2. customThe organic fraction was separated
  3. washwashed with water
  4. dry with materialthen dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customto give an oil which

Sources & evidence

ORD record
ord-70f63e3063294df49c4f23fba21f2219
Source dataset
uspto-grants-2001_08
Patent number
US06274632B1

Reaction notes

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