Methanesulfonyl chloride → HCID 54083760, compound

HRID 620926Notes

Reaction equation

HRID 620926 reaction equation
[CH3:1][C:2]([NH:8][C:9](=[O:18])[C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[C:12]([Cl:17])[CH:11]=1)([CH3:7])[C:3]([CH2:5][OH:6])=[O:4].C(N(C(C)C)CC)(C)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl>[CH3:7][C:2]([NH:8][C:9](=[O:18])[C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[C:12]([Cl:17])[CH:11]=1)([CH3:1])[C:3]([CH2:5][O:6][S:29]([CH3:28])(=[O:31])=[O:30])=[O:4]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 54349857HCID 54349857, compound

Product 1

HCID 54083760HCID 54083760, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-(1',1'-dimethyl-3'-hydroxyacetonyl)-3,5-dichlorobenzamide (1.0 gm, 0.00345 m) was dissolved in methylene chloride (25 ml) and diisopropylethylamine (0.44 gm, 0.0035 m) and cooled to about 5° C. under a nitrogen atmosphere. While the solution was stirred magnetically, methanesulfonylchloride (0.475 gm, 0.0041 m) was added dropwise. After its addition, the mixture was stirred about an hour longer while maintaining the temperature at 5°-10° C. The mixture was then poured into ice water (500 ml) containing methylene chloride (100 ml). The organic layer was separated and was washed with cold 1% hydrochloric acid, saturated sodium bicarbonate, water and brine, and then dried over anhydrous potassium carbonate. The solvent was removed and 800 mg of the desired product was obtained.

Workup

  1. additionAfter its addition
  2. stirringthe mixture was stirred about an hour longer
  3. temperaturewhile maintaining the temperature at 5°-10° C
  4. customThe organic layer was separated
  5. washwas washed with cold 1% hydrochloric acid, saturated sodium bicarbonate, water and brine
  6. dry with materialdried over anhydrous potassium carbonate
  7. customThe solvent was removed

Sources & evidence

ORD record
ord-8ff6e4aabd2d4b65b8865e341566f812
Source dataset
uspto-grants-1989_04
Patent number
US04822902

Reaction notes

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