Lawesson's reagent → (E)-Ethyl 3-[6-[[3,5-bis(trimethylsilyl)benzenecarbothioyl]amino]pyridin-3-yl]acrylate

HRID 2265113Notes

Reaction equation

HRID 2265113 reaction equation
[CH3:1][Si:2]([CH3:30])([CH3:29])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([Si:25]([CH3:28])([CH3:27])[CH3:26])[CH:24]=1)[C:6]([NH:8][C:9]1[N:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=1)=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:40])=CC=1.C[Si](C)(C)C1C=C(C(NC2C=CC(C=CC(OCC)=O)=CC=2)=S)C=C([Si](C)(C)C)C=1>>[CH3:1][Si:2]([CH3:30])([CH3:29])[C:3]1[CH:4]=[C:5]([C:6]([NH:8][C:9]2[N:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=2)=[S:40])[CH:22]=[C:23]([Si:25]([CH3:28])([CH3:27])[CH3:26])[CH:24]=1

Participants

4

Reactant 3

HCID 87949Lawesson's reagentHCID 86644273(E)-Ethyl 3-[6-[[3,5-bis(trimethylsilyl)benzoyl]amino]pyridin-3-yl]acrylateHCID 86644287Ethyl 4-[[3,5-bis(trimethylsilyl)benzenecarbothioyl]amino]cinnamate

Product 1

HCID 86644288(E)-Ethyl 3-[6-[[3,5-bis(trimethylsilyl)benzenecarbothioyl]amino]pyridin-3-yl]acrylateYield 92.6%

Procedure

Using Compound 18a (135 mg) and Lawesson's reagent (86.7 mg), Compound 18b (90.7 mg, 65%) was obtained as a yellow solid in the same manner as Compound 17b was synthesized.

Sources & evidence

ORD record
ord-ac54bc79ab454b0891e405f8a3689c7c
Source dataset
uspto-grants-2010_12
Patent number
US07855300B2

Reaction notes

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