Acetyl chloride → HCID 70373580, compound

HRID 1709295Notes

Reaction equation

HRID 1709295 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[C:5]([C:9]1[CH:27]=[CH:26][C:12]([CH2:13][CH2:14][NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])=[CH:11][CH:10]=1)(=[O:8])[CH2:6][CH3:7].C(N(CC)CC)C>C(Cl)Cl>[C:5]([C:9]1[CH:27]=[CH:26][C:12]([CH2:13][CH2:14][N:15]([C:1](=[O:3])[CH3:2])[S:16]([C:19]2[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=2)(=[O:17])=[O:18])=[CH:11][CH:10]=1)(=[O:8])[CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 13826015HCID 13826015, compound

Product 1

HCID 70373580HCID 70373580, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3.57 g. (45.5 mmole) acetyl chloride in 50 ml. methylene chloride is slowly added dropwise to an ice-cold mixture of 16.0 g. (45.5 mmole) 4-chlorobenzenesulphonic acid-(4-propionylphenethylamide), 5.1 ml. (50 mmole) triethylamine and 200 ml. methylene chloride. The reaction mixture is then stirred for 3 hours at ambient temperature, extracted with 2N hydrochloric acid and several times with water, dried with anhydrous sodium sulphate and evaporated. After chromatography with silica gel/toluene +ethyl acetate (12:1 v/v), there are obtained 10.2 g. (57% of theory) of the desired product; m.p. 91°-92° C. (after recrystallisation from heptane +toluene).

Workup

  1. extractionextracted with 2N hydrochloric acid and several times with water
  2. dry with materialdried with anhydrous sodium sulphate
  3. customevaporated
  4. customAfter chromatography with silica gel/toluene +ethyl acetate (12:1 v/v), there are obtained 10.2 g

Sources & evidence

ORD record
ord-5410ef6a308b478390ac4e80771897d3
Source dataset
uspto-grants-1990_08
Patent number
US04948809

Reaction notes

Loading…