Trichloromethanesulfenyl chloride → HCID 131711935, compound

HRID 904132Notes

Reaction equation

HRID 904132 reaction equation
[CH3:1][C:2]1([CH3:14])[CH:13]=[CH:12][C:5]2[CH2:6][C:7]([NH:9][C:10](=[O:11])[C:4]=2[CH2:3]1)=[O:8].[H-].[Na+].[Cl:17][C:18]([Cl:22])([Cl:21])[S:19]Cl>O1CCCC1.CCCCCC>[Cl:17][C:18]([Cl:22])([Cl:21])[S:19][N:9]1[C:10](=[O:11])[C:4]2[CH2:3][C:2]([CH3:14])([CH3:1])[CH:13]=[CH:12][C:5]=2[CH2:6][C:7]1=[O:8]

Participants

6

Reactant 3

HCID 11666Trichloromethanesulfenyl chlorideHCID 24758Sodium hydrideHCID 131711936HCID 131711936, compound

Product 1

HCID 131711935HCID 131711935, compoundYield 32.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To 4,4-dimethyl homophthalimide (5.6 g) in 200 ml dry tetrahydrofuran was added 1.73 g sodium hydride. The mixture was stirred for one hour, then 5.75 g (3.38 ml) trichloromethyl sulfenyl chloride was added dropwise. The mixture was refluxed overnight, stripped of solvent, slurried in hexane and decanted. The brown crystalline residue was purified by tlc and recrystallized in ethanol to yield 3.2 g of the brown crystalline product, m.p. 129°-130° C.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customdecanted
  3. customThe brown crystalline residue was purified by tlc
  4. customrecrystallized in ethanol

Sources & evidence

ORD record
ord-3d65cd1d29f445888b8524334594f192
Source dataset
uspto-grants-1980_10
Patent number
US04230711

Reaction notes

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