1,1,2,2-Tetrachloroethylsulfenyl chloride → HCID 131711937, compound

HRID 904133Notes

Reaction equation

HRID 904133 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].[Cl:15][C:16]([Cl:22])([S:20]Cl)[CH:17]([Cl:19])[Cl:18]>C(N(CC)CC)C>[Cl:15][C:16]([Cl:22])([S:20][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])[CH:17]([Cl:19])[Cl:18]

Participants

4

Reactant 2

HCID 144531,1,2,2-Tetrachloroethylsulfenyl chlorideHCID 131711936HCID 131711936, compound

Product 1

HCID 131711937HCID 131711937, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a 200-ml methylene solution of 4,4-dimethylhomophthalimide (33.5 g) and 1,1,2,2-tetrachloroethyl sulfenyl chloride (42.2 g) at 0° C. was added dropwise 18.2 g triethylamine over 5 minutes. The mixture was stirred for 4 hours, washed with 200 ml water and dried (MgSO4). The solvent was evaporated and a brown oil was recovered, recrystallized in ethanol to yield 54 g (78%) tan solid, m.p. 112°-113° C.

Workup

  1. washwashed with 200 ml water
  2. dry with materialdried (MgSO4)
  3. customThe solvent was evaporated
  4. customa brown oil was recovered
  5. customrecrystallized in ethanol

Sources & evidence

ORD record
ord-3e15dd91e10f4725a615ec51c314e2ef
Source dataset
uspto-grants-1980_10
Patent number
US04230711

Reaction notes

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