Dimethyl Sulfoxide → HCID 20199150, compound

HRID 652093Notes

Reaction equation

HRID 652093 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH3:11][N:12]1[C:16]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][N:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[CH:24]=2)=[N:15][C:14]([CH2:36][OH:37])=[N:13]1>ClCCl>[CH3:11][N:12]1[C:16]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][N:30]3[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]3)[CH:24]=2)=[N:15][C:14]([CH:36]=[O:37])=[N:13]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 20199146HCID 20199146, compound

Product 1

HCID 20199150HCID 20199150, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dimethyl sulphoxide (304 mg) was added to a solution of oxalyl chloride (254 mg) in dichloromethane (20 ml) at -60° under nitrogen for 2 min. and a solution of 1-methyl-5-[[4-[3-(1-piperidinylmethyl)phenoxy]butyl]amino]-1H-1,2,4-triazole-3-methanol (0.5 g) in dichloromethane (10 ml) was added. The mixture was stirred at -50° to -60° for 15 min. and then quenched with triethylamine (657 mg). The solution was allowed to warm to 25° and was diluted with water. The aqueous phase was extracted with dichloromethane and the combined organic extracts were dried and evaporated to leave the title compound as a pale yellow oil (0.4 g).

Workup

  1. customquenched with triethylamine (657 mg)
  2. temperatureto warm to 25°
  3. additionwas diluted with water
  4. extractionThe aqueous phase was extracted with dichloromethane
  5. customthe combined organic extracts were dried
  6. customevaporated

Sources & evidence

ORD record
ord-87161d44bc054dccad50c2b5087a41ca
Source dataset
uspto-grants-1987_06
Patent number
US04670448

Reaction notes

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