Water → HCID 178527774, compound

HRID 2297525Notes

Reaction equation

[C:1]1([CH:7]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][C:17]3[C:18](O)=[N:19][C:20]4[C:25]([N:26]=3)=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:43])=CC=1.O>C1COCC1>[C:1]1([CH:7]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][C:17]3[C:18]([SH:43])=[N:19][C:20]4[C:25]([N:26]=3)=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 60 °C

Procedure

3-(3-(4-(diphenylmethyl)piperidyl)propyl)quinoxaline-2-ol (257 mg) was dissolved in THF, and Lawesson's reagent (200 mg) was added to the solution, followed by stirring the mixture at 60° C. for 8 hours. Then Lawesson's reagent (110 mg) was further added and the mixture was stirred at 60° C. for 8 hours. Water was added to the mixture and then the mixture was extracted with dichloromethane. Organic layers were combined and washed with brine. The resultant was dried over anhydrous sodium: sulfate and the residue was purified by (ethanol:ethyl acetate=10:1) to obtain 103 mg of 3-(3-(4-(diphenylmethyl)piperidyl)propyl)quinoxaline-2-thiol. Yield: 39%.

Workup

stirringthe mixture was stirred at 60° C. for 8 hours
extractionthe mixture was extracted with dichloromethane
washwashed with brine
dry with materialThe resultant was dried over anhydrous sodium
customsulfate and the residue was purified by (ethanol:ethyl acetate=10:1)

Sources & evidence

ORD record: ord-4ac45c7d9a4146759b59592f66650128
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492364B1

Reaction notes

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