Methanesulfonyl chloride → HCID 22118429, compound

HRID 1275466Notes

Reaction equation

HRID 1275466 reaction equation
[CH3:1][C:2]1([CH3:21])[CH:11]([OH:12])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]=2[CH3:13])[S:4](=[O:20])(=[O:19])[CH2:3]1.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>N1C=CC=CC=1>[CH3:21][C:2]1([CH3:1])[CH:11]([O:12][S:23]([CH3:22])(=[O:25])=[O:24])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]=2[CH3:13])[S:4](=[O:20])(=[O:19])[CH2:3]1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 22118465HCID 22118465, compound

Product 1

HCID 22118429HCID 22118429, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4.1 Grams (13 mmol)of 3,3,5-trimethyl-4-hydroxy-6-ethoxycarbonylthiochroman-1,1-dioxide was dissolved in 15 ml of pyridine, and the mixture was cooled in an ice bath. 1.8 Grams (16 mmol, 1.2 eq.) of methanesulfonyl chloride was gradually added thereto. After the addition, the ice bath was removed, and the mixture was allowed to stand overnight. The reaction mixture was diluted with 200 ml of ethyl acetate, and washed with 200 ml of water, with 150 ml of a 1 wt % hydrochloric acid aqueous solution twice, with 150 ml of a saturated sodium hydrogencarbonate aqueous solution and with 50 ml of water in this order. An organic layer was dried over sodium sulfate, the solvent was distilled off, and the residue was dried under reduced pressure to give 4.9 g (yield 97%) of a brownish oil. The brownish oil solidified after allowed to stand overnight.

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. additionAfter the addition
  3. customthe ice bath was removed
  4. additionThe reaction mixture was diluted with 200 ml of ethyl acetate
  5. washwashed with 200 ml of water, with 150 ml of a 1 wt % hydrochloric acid aqueous solution twice
  6. dry with materialAn organic layer was dried over sodium sulfate
  7. distillationthe solvent was distilled off
  8. customthe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-ca46e2a463cc450bbb39f798a06fa7d0
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

Loading…