Triethylamine → HCID 86666149, compound

HRID 707648Notes

Reaction equation

HRID 707648 reaction equation
[OH:1][CH2:2][C:3]1[S:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[N:5][N:4]=1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>ClCCl>[CH3:21][S:22]([O:1][CH2:2][C:3]1[S:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[N:5][N:4]=1)(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58504238HCID 58504238, compound

Product 1

HCID 86666149HCID 86666149, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 2-(5-hydroxymethyl-1,3,4-thiadiazol-2-yl)-pyridine (6 gm), and triethylamine (13.1 ml) in dichloromethane (150 ml) was added methanesulfonylchloride (5.31 gm) at 0° C. The reaction mixture was stirred at 0° C. over a period of 1 h. The reaction was quenched by addition of water and layers were separated. Aqueous layer was extracted with dichloromethane (50 ml×2). Combined organic layer was washed with aqueous sodium bicarbonate solution followed by water and evaporated under vacuum to provide title compound in 7.5 gm quantity (88%) as oil.

Workup

  1. customThe reaction was quenched by addition of water and layers
  2. customwere separated
  3. extractionAqueous layer was extracted with dichloromethane (50 ml×2)
  4. washCombined organic layer was washed with aqueous sodium bicarbonate solution
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-23759aff44de4edd994347a3856e5beb
Source dataset
uspto-grants-2015_11
Patent number
US09175031B2

Reaction notes

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