Dimethyl Sulfoxide → HCID 57508940, compound

HRID 2240840Notes

Reaction equation

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

Participants

Conditions

Temperature: -40 °C

Procedure

To a cold solution (−70° C.) of oxalyl chloride (169 mg, 1.34 mmol) and DMSO (209 mg, 2.67 mmol) in DCM (4 mL) a solution of {4-[5-(3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-methanol (410 mg, 1.11 mmol) in DCM (5 mL) is added. The mixture is warmed to −40° C. within 30 min and then triethylamine (394 mg, 3.89 mmol) is added. Stirring is continued at −40° C. for 1 h, then at rt. The reaction is quenched by adding water and the mixture is extracted with diethyl ether. The organic extract is dried over MgSO4, filtered and the solvent of the filtrate is evaporated. The crude product is purified by chromatography on prep. TLC plates with heptane:EA 3:1 to give 4-[5-(3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-[1,2,4]oxadiazol-3-yl]-benzaldehyde (180 mg) as a white solid; LC-MS: tR=1.24 min, [M+1]+=367.24.

Workup

customat rt
customThe reaction is quenched
additionby adding water
extractionthe mixture is extracted with diethyl ether
extractionThe organic extract
dry with materialis dried over MgSO4
filtrationfiltered
customthe solvent of the filtrate is evaporated
customThe crude product is purified by chromatography on prep

Sources & evidence

ORD record: ord-28f20a625320488eb86c96ed00e3112d
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723378B2

Reaction notes

Loading…