Triethylamine → 1,2,3-Thiadiazole-5-methanol, 4-methyl-, 5-methanesulfonate

HRID 992683Notes

Reaction equation

HRID 992683 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[OH:13][CH2:14][C:15]1[S:19][N:18]=[N:17][C:16]=1[CH3:20].O.ClCCl>ClCCl>[CH3:8][S:9]([O:13][CH2:14][C:15]1[S:19][N:18]=[N:17][C:16]=1[CH3:20])(=[O:11])=[O:10]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18411623(4-Methyl-1,2,3-thiadiazol-5-yl)methanolHCID 21908982Water methylene chloride

Product 1

HCID 184116401,2,3-Thiadiazole-5-methanol, 4-methyl-, 5-methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under nitrogen atmosphere, 10.0 ml of triethylamine (72.6 m mol) and 4.1 ml of methanesulfonyl chloride (53 m mol) was added successively to a solution of 6.27 g of 5-hydroxymethyl-4-methyl-1,2,3-thiadiazole (48.16 m mol) in dichloromethane (50 ml) at −30° C. After stirring for 30 minutes, the mixture was poured into water-dichloromethane while the pH was kept between 8.5-9.0. The aqueous layer was separated, the organic layer was washed with saturated sodium hydrocarbonate, washed with dil-hydrochloric acid brine, dried over magnesium sulfate. After filtration, the filtrate was concentrated in vacuo to afford 5-methanesulfonyloxymethyl-4-methyl-1,2,3-thiadiazol (9.8 g).

Workup

  1. customThe aqueous layer was separated
  2. washthe organic layer was washed with saturated sodium hydrocarbonate
  3. washwashed with dil-hydrochloric acid brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e813c20e4e634bbf89c954f7448e17d4
Source dataset
uspto-grants-2002_10
Patent number
US06468995B1

Reaction notes

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