Carbon Tetrachloride → HCID 15616511, compound

HRID 255837Notes

Reaction equation

HRID 255837 reaction equation
O[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])=[O:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:38]>>[Cl:38][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])=[O:11]

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 138229722-(2-hydroxyethyl)-N-(1,1-dimethylethyl)benzenesulfonamide

Product 1

HCID 15616511HCID 15616511, compound

Procedure

A solution of 32.5 g of the alcohol from Example 1 and 32.5 g triphenylphosphine in 244 ml of carbon tetrachloride was stirred at room temperature and under an atmosphere of nitrogen for 72 hours. Excess carbon tetrachloride was removed in vacuo to give 83 g of a crude yellow oil. Purification by silica gel chromatography (hexanes-20% ethyl acetate) afforded a colorless viscous oil which crystallized on standing. The product was isolated by trituration with hexanes, filtration, and drying. The yield of pure 2-(2-chloroethyl)-N-(1,1-dimethylethyl)benzenesulfonamide, m.p. 64°-65° C., was 15.9 g.

Workup

  1. customExcess carbon tetrachloride was removed in vacuo
  2. customto give 83 g of a crude yellow oil
  3. customPurification by silica gel chromatography (hexanes-20% ethyl acetate)
  4. customafforded a colorless viscous oil which
  5. customcrystallized
  6. customThe product was isolated by trituration with hexanes, filtration
  7. customdrying

Sources & evidence

ORD record
ord-8995a58f21544f10be84711d3dbf6e80
Source dataset
uspto-grants-1987_10
Patent number
US04699650

Reaction notes

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