Acetic Anhydride → HCID 15118095, compound

HRID 476526Notes

Reaction equation

HRID 476526 reaction equation
[CH3:1][N:2]([CH2:17][C:18]([NH2:20])=[O:19])[S:3]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1)(=[O:5])=[O:4].[C:21](OC(=O)C)(=[O:23])[CH3:22]>S(=O)(=O)(O)O>[C:21]([NH:20][C:18](=[O:19])[CH2:17][N:2]([CH3:1])[S:3]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:14])[F:15])[CH:8]=1)(=[O:5])=[O:4])(=[O:23])[CH3:22]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 15118086HCID 15118086, compound

Product 1

HCID 15118095HCID 15118095, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
138 °C

Procedure

In this example, a catalytic amount (about 4 drops) of concentrated sulfuric acid was added to a suspension of 3.5 g of (N-methyl-3-trifluoromethylbenzylsulfonamido)-acetamide in 7 mls (7.6 g) of acetic anhydride at room temperature. The mixture was heated for 2 hours at about 138° C. and then poured into ice water and extracted into methylene chloride. The methylene chloride extract was washed with aqueous 5 wt.% sodium bicarbonate solution, dried over magnesium sulfate and evaporated to dryness affording 3.4 g of a white solid. The solid was triturated with ethyl ether affording 2.17 g of the title compound.

Workup

  1. extractionextracted into methylene chloride
  2. extractionThe methylene chloride extract
  3. washwas washed with aqueous 5 wt.% sodium bicarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-5bd28dae542c40979b0bc70f8e43a56f
Source dataset
uspto-grants-1989_12
Patent number
US04885027

Reaction notes

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