Carbon Tetrachloride → 2-(2-Chloroethyl)-N-(1,1-dimethylethyl)benzenesulfonamide

HRID 2118456Notes

Reaction equation

HRID 2118456 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 156165112-(2-Chloroethyl)-N-(1,1-dimethylethyl)benzenesulfonamide

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-563576dc87eb4130b82fe324908c985f
Source dataset
uspto-grants-1987_07
Patent number
US04678502

Reaction notes

Loading…