1H-benzimidazole-5-carbohydrazide → HCID 178492804, compound

HRID 710521Notes

Reaction equation

HRID 710521 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([NH:12][NH2:13])=[O:11])=[CH:9][C:4]=2[NH:3][CH:2]=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([S:24]([CH2:27][C:28](O)=S)(=[O:26])=[O:25])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]>>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([S:24]([CH2:27][C:28]2[O:11][C:10]([C:8]3[CH:7]=[CH:6][C:5]4[NH:1][CH:2]=[N:3][C:4]=4[CH:9]=3)=[N:12][N:13]=2)(=[O:26])=[O:25])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]

Participants

3

Reactant 2

HCID 166371191H-benzimidazole-5-carbohydrazideHCID 178492809HCID 178492809, compound

Product 1

HCID 178492804HCID 178492804, compound

Procedure

The compound was synthesized starting from benzimidazol-5-carbohydrazide (176 mg, 1 mmol) and 3,4-dimethoxyphenylsulfonylthioacetic acid (261 mg; 1 mmol) as described in method 2 but purified by flash chromatography on silica using a CHCl3/MeOH gradient; yield: 0.022 g (5.5%); MS m/z: 401.2 [M+H]+; 1H-NMR (DMSO d6, 400 MHz): δ 3.75 (s, 3H); 3.82 (s, 3H); 5.29 (s, 2H); 7.15 (d, 1H3J=8.7 Hz); 7.328-7.333 (m, 1H); 7.38 (dd, 1H, 4J=2.1 Hz, 3J=8.7 Hz); 7.68-7.72 (m, 1H); 7.78-7.82 (m, 1H); 8.01 (br s, 1H); 8.38 (s, 1H); 12.80 (br s, 1H); HPLC (METHOD [A]): rt 10.19 min (90.6%)

Workup

  1. customThe compound was synthesized
  2. custompurified by flash chromatography on silica using a CHCl3/MeOH gradient
  3. customrt 10.19 min (90.6%)

Sources & evidence

ORD record
ord-81fe628556db40a9a54c5a0117afd307
Source dataset
uspto-grants-2015_11
Patent number
US09181233B2

Reaction notes

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