Dimethyl Sulfoxide → HCID 178474986, compound

HRID 1961657Notes

Reaction equation

HRID 1961657 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][CH2:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([NH:20][C:21](=[O:23])[CH3:22])[CH2:16][CH2:15]1.CCN(CC)CC>C(Cl)Cl.O.C(Cl)Cl.CO>[O:11]=[CH:12][CH2:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([NH:20][C:21](=[O:23])[CH3:22])[CH2:16][CH2:15]1

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 178474987HCID 178474987, compound

Product 1

HCID 178474986HCID 178474986, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×HCID 21226129Dichloromethane methanolSolvent

Procedure

DMSO (3.68 g, 47 mmol) in CH2Cl2 (20 ml) was added at −78° C. to a stirred solution of oxalylchloride (2.9 g, 23 mmol) in CH2Cl2 (100 ml). After 1 h stirring at −78° C. a solution of N-[trans-4-(2-hydroxy-ethyl)-cyclohexyl]-acetamide (2.18 g, 12 mmol) in CH2Cl2 (80 ml) was added followed after 2 h by Et3N (7.14 g, 71 mmol). The mixture was allowed to reach room temperature and was then diluted with H2O and extracted with CH2Cl2. The combined organic layers were dryed (Na2SO4) and the solvent was evaporated to afford the crude product. Chromatography (CH2Cl2/MeOH 95:5) yielded 1.75 g (81%, 9.5 mmol) of a light brown solid. MS (m/z): 184.3 ([M+H])+.

Workup

  1. additionwas added
  2. customto reach room temperature
  3. extractionextracted with CH2Cl2
  4. customthe solvent was evaporated
  5. customto afford the crude product

Sources & evidence

ORD record
ord-a56a9a59839c44dc808e5d145256596b
Source dataset
uspto-grants-2013_04
Patent number
US08415350B2

Reaction notes

Loading…