Acetic Anhydride → HCID 15616509, compound

HRID 622301Notes

Reaction equation

HRID 622301 reaction equation
[OH:1][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].C(N(CC)CC)C.[C:25](OC(=O)C)(=[O:27])[CH3:26]>ClCCl>[C:25]([O:1][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])(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 138229722-(2-hydroxyethyl)-N-(1,1-dimethylethyl)benzenesulfonamide

Product 1

HCID 15616509HCID 15616509, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 29.0 g of the product from Example 1 and 24 ml triethylamine in 290 ml of dichloromethane was cooled to 0° C. and treated with 13 ml acetic anhydride. The reaction mixture was stirred at room temperature for 22 hours. Dichloromethane (200 ml) was added and the organic layer washed with three 50 ml portions of water and one portion of brine. Drying the organic layer over magnesium sulfate followed by concentrating in vacuo gave the crude product. Purification by silica gel chromatography (elution with hexanes-ethyl acetate, 70:30) afforded 19.5 g of pure 2-[2-(acetyloxy)ethyl]-N-(1,1-dimethylethyl)benzenesulfonamide as a colorless oil.

Workup

  1. washthe organic layer washed with three 50 ml portions of water and one portion of brine
  2. dry with materialDrying the organic layer over magnesium sulfate
  3. concentrationby concentrating in vacuo
  4. customgave the crude product
  5. customPurification
  6. washby silica gel chromatography (elution with hexanes-ethyl acetate, 70:30)

Sources & evidence

ORD record
ord-c27c564a985341bf980cba9fab070e75
Source dataset
uspto-grants-1988_09
Patent number
US04770690

Reaction notes

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