Lawesson's reagent → HCID 57476016, compound

HRID 1960283Notes

Reaction equation

[CH2:1]([N:3]([S:17]([C:20]1[S:21][CH:22]=[CH:23][CH:24]=1)(=[O:19])=[O:18])[C:4]1[CH:5]=[CH:6][C:7]([CH3:16])=[C:8]2[C:12]=1[NH:11][C:10]([C:13]([NH2:15])=O)=[CH:9]2)[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:34])=CC=1>O1CCCC1>[CH2:1]([N:3]([S:17]([C:20]1[S:21][CH:22]=[CH:23][CH:24]=1)(=[O:19])=[O:18])[C:4]1[CH:5]=[CH:6][C:7]([CH3:16])=[C:8]2[C:12]=1[NH:11][C:10]([C:13](=[S:34])[NH2:15])=[CH:9]2)[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 7-[ethyl(2-thienylsulfonyl)amino]-4-methyl-1H-indole-2-carboxamide (1.9 g), Lawesson's reagent (2.1 g) and tetrahydrofuran (100 ml) was stirred at 40° C. for 4 hr. The reaction solution was concentrated under reduced pressure, and the obtained oil was crystallized from dichloromethane-toluene, and washed with toluene to give 7-[ethyl(2-thienylsulfonyl)amino]-4-methyl-1H-indole-2-carbothioamide (2.0 g, yield quantitative) as pale-yellow crystals. A solution of the obtained crystals (2.0 g) and bromomalonaldehyde (2.4 g) in N,N-dimethylacetamide (50 ml) was stirred at 70° C. for 3 hr. The reaction solution was diluted with ethyl acetate, washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained oil was crystallized from dichloromethane-toluene to give the title compound (1.6 g, yield 70%) as pale-yellow crystals.

Workup

concentrationThe reaction solution was concentrated under reduced pressure
customthe obtained oil was crystallized from dichloromethane-toluene
washwashed with toluene

Sources & evidence

ORD record: ord-67163b90eece4aec97892e64214bef42
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410087B2

Reaction notes

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