Thiophenol → HCID 19347986, compound

HRID 1637197Notes

Reaction equation

N12CCCN=C1CCCCC2.[CH2:12]([O:19][C:20]1[CH:21]=[CH:22][C:23]2[C:27](Cl)=[C:26]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[S:25][C:24]=2[CH:34]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:35]1([SH:41])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CN(C)C=O>[CH2:12]([O:19][C:20]1[CH:21]=[CH:22][C:23]2[C:27]([S:41][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[C:26]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[S:25][C:24]=2[CH:34]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 60 °C

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU--0.39 ml, 2.5 mmol) was added to a mixture of ethyl 6-(benzyloxy)-3-chlorobenzo[b]thiophene-2-carboxylate (Preparation 8, 800 mg, 2.3 mmol) and thiophenol (0.47 ml, 4.6 mmol) in dimethylformamide (4 ml) under a nitrogen atmosphere. The solution was heated to 60° C. for 6 hours and then partitioned between diethyl ether and water. The organics were separated and washed with water, dried (magnesium sulfate) and evaporated under reduced pressure. The residue was flash chromatographed on silica gel using a mixture of 20% dichloromethane and 80% hexane, then 50% dichloromethane and 50% hexane as eluant. The isolated product was crystallised from diisopropyl ether and hexane to give the title compound as a colourless solid (810 mg).

Workup

custompartitioned between diethyl ether and water
customThe organics were separated
washwashed with water
dry with materialdried (magnesium sulfate)
customevaporated under reduced pressure
customchromatographed on silica gel using
additiona mixture of 20% dichloromethane and 80% hexane
customThe isolated product was crystallised from diisopropyl ether and hexane

Sources & evidence

ORD record: ord-176968daee0b4d0b8f52c5d64139baf1
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06040309

Reaction notes

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