Lawesson's reagent → HCID 178490026, compound

HRID 710523Notes

Reaction equation

HRID 710523 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([NH:12][NH2:13])=O)=[CH:9][C:4]=2[NH:3][CH:2]=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH2:24][CH2:25][C:26](Cl)=O)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:38])=CC=1>>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH2:24][CH2:25][C:26]1[S:38][C:10]([C:8]2[CH:7]=[CH:6][C:5]3[NH:1][CH:2]=[N:3][C:4]=3[CH:9]=2)=[N:12][N:13]=1

Participants

4

Reactant 3

HCID 87949Lawesson's reagentHCID 156207023-(3,4-Dimethoxyphenyl)propionyl chlorideHCID 166371191H-benzimidazole-5-carbohydrazide

Product 1

HCID 178490026HCID 178490026, compound

Procedure

The compound was synthesized starting from benzimidazol-5-carbohydrazide (176 mg; 1 mmol), TEA (0.153 ml; 1.1 mmol), 3,4-dimethoxyphenylpropionylchloride (228 mg, 1.1 mmol) and Lawesson's reagent (606 mg; 1.5 mmol) as described in method 1; yield: 0.017 g (4.6%); MS m/z: 367.2 [M+H]+; 1H-NMR (DMSO d6, 400 MHz): δ 3.00 (t, 2H, 3J=7.5 Hz); 3.40 (t, 2H, 3J=7.5 Hz); 3.68 (s, 3H); 3.70 (s, 3H); 6.75-6.77 (m, 1H); 6.81-6.83 (m, 1H); 6.89 (br s, 1H); 7.67-7.69 (m, 1H); 7.73-7.75 (m, 1H); 8.09 (br s, 1H); 8.34 (s, 1H; HPLC (METHOD [A]): rt 10.82 min (100%)

Workup

  1. customThe compound was synthesized
  2. customrt 10.82 min (100%)

Sources & evidence

ORD record
ord-06114f56c8e141299854404d4f4136c9
Source dataset
uspto-grants-2015_11
Patent number
US09181233B2

Reaction notes

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