Lawesson's reagent → HCID 10383968, compound

HRID 844129Notes

Reaction equation

HRID 844129 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=3)[CH:15]=[CH:16][C:11]=2[NH:10][C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:36])=CC=1>>[CH2:1]([N:8]1[C:12]2[CH:13]=[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=3)[CH:15]=[CH:16][C:11]=2[NH:10][C:9]1=[S:36])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 87949Lawesson's reagentHCID 9906170HCID 9906170, compound

Product 1

HCID 10383968HCID 10383968, compound

Procedure

Prepared according to the procedure for Example 24 from 1-benzyl-6-(3-nitrophenyl)-1,3-dihydro-2H-benzimidazole-2-one (0.1 g, 0.29 mmol) and Lawesson's reagent (0.13 g, 0.32 mmol). A yellow solid (0.025 g, 24%): mp 244-245° C.; 1H-NMR (DMSO-d6) δ13.08 (s, 1H), 8.43 (s, 1H), 8.20 (dd, 1H, J=8.2, 1.7 Hz), 8.12 (d, 1H, J=7.8 Hz), 7.72-7.78 (m, 2H), 7.62 (d, 1H, J=8.3 Hz), 7.25-7.43 (m, 6H), 5.62 (s, 2H); MS (ESI) m/z 360 [M−H]−; Anal. Calc. For C20H15ClN2S.0.2H2O: C, 65.81; H, 4.25; N, 11.51. Found: C, 65.56; H, 4.11; N, 11.29.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-0ace48b92e944a7885675c53766fe90e
Source dataset
uspto-grants-2002_04
Patent number
US06380235B1

Reaction notes

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