Dimethyl Sulfoxide → N-(6-benzyloxy-3-hydroxy-2,2-dimethylchroman-4-yl)-N-methyl-methanesulfonamide

HRID 613438Notes

Reaction equation

C[CH2:2][S:3]([NH2:6])(=[O:5])=[O:4].[H-].[Na+].[CH2:9]([O:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[O:23][C:22]([CH3:28])([CH3:27])[CH:21]1[O:29][CH:20]21)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O.[CH3:31]S(C)=O>>[CH2:9]([O:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[O:23][C:22]([CH3:28])([CH3:27])[CH:21]([OH:29])[CH:20]2[N:6]([CH3:31])[S:3]([CH3:2])(=[O:5])=[O:4])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Reactant 5

HCID 679Dimethyl Sulfoxide3×

HCID 962Water

HCID 24758Sodium hydride

HCID 73702Ethanesulfonamide

HCID 109240076-Benzyloxy-2,2-dimethyl-3,4-epoxychroman

Product 1

HCID 11760985N-(6-benzyloxy-3-hydroxy-2,2-dimethylchroman-4-yl)-N-methyl-methanesulfonamide

Procedure

4.25 g (39 mmol) of methyl-methanesulfonamide in 7.5 ml of DMSO were added dropwise to a suspension of 0.21 g (7 mmol) of 80 percent sodium hydride in 15 ml of DMSO, and the mixture was stirred at RT for 30 min. 8.2 g (29 mmol) of 6-benzyloxy-2,2-dimethyl-3,4-epoxychroman, dissolved in 18 ml of DMSO were then added dropwise, and the batch was heated at 50° C. for 2 days. The mixture was subsequently poured into water and the precipitate was filtered off with suction and dried well under reduced pressure, giving 8.8 g of N-(6-benzyloxy-3-hydroxy-2,2-dimethylchroman-4-yl)-N-methyl-methanesulfonamide, m.p. 162-164° C.

Workup

additionwere then added dropwise
temperaturethe batch was heated at 50° C. for 2 days
filtrationthe precipitate was filtered off with suction
customdried well under reduced pressure

Sources & evidence

ORD record: ord-69eed1fccb93400196360b396b1b4e8c
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06008245

Reaction notes

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