Triethylamine → HCID 86706843, compound

HRID 707660Notes

Reaction equation

HRID 707660 reaction equation
[OH:1][CH:2]([C:4]1[S:8][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[N:6][N:5]=1)[CH3:3].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>ClCCl>[CH3:22][S:23]([O:1][CH:2]([C:4]1[S:8][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[N:6][N:5]=1)[CH3:3])(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67960301HCID 67960301, compound

Product 1

HCID 86706843HCID 86706843, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (RS)-2-(5-(1-hydroxy-ethyl)-1,3,4-thiadiazol-2-yl)-pyridine (1.0 gm), and triethylamine (2 ml) in dichloromethane (50 ml) was added methanesulfonyl chloride (0.9 gm) at −10° C. The reaction mixture was stirred over a period of 1 h. The reaction was quenched by addition of water and layers were separated. Aqueous layer was extracted with dichloromethane. Combined organic layer was washed with aqueous sodium bicarbonate followed by water and evaporated under vacuum to provide the title compound in 1.0 gm quantity (73%) as an oil.

Workup

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

Sources & evidence

ORD record
ord-7e35df853ff54e85b595c464eccb1005
Source dataset
uspto-grants-2015_11
Patent number
US09175031B2

Reaction notes

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