Phosphorus oxychloride → HCID 178490062, compound

HRID 710512

Reaction equation

HRID 710512 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[C:21]([O:22][CH3:23])=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:24][CH2:25][C:26](Cl)=O.O=P(Cl)(Cl)Cl>>[CH3:14][O:15][C:16]1[C:21]([O:22][CH3:23])=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:24][CH2:25][C:26]1[O:11][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 24813Phosphorus oxychlorideHCID 110751782,3-DimethoxyphenylpropionylchlorideHCID 166371191H-benzimidazole-5-carbohydrazide

Product 1

HCID 178490062HCID 178490062, compound

Procedure

The compound was synthesized starting from benzimidazol-5-carbohydrazide (176 mg, 1 mmol), TEA (0.153 ml; 1.1 mmol), 2,3-dimethoxyphenylpropionylchloride (228 mg, 1.1 mmol) and POCl3 (0.5 ml; 5.5 mmol) as described in method 1; yield: 0.016 mg (4.6%); MS m/z; 351.3 [M+H]+; 1H-NMR (DMSO d6, 400 MHz): δ 3.06-3.10 (m, 2H); 3.17-3.21 (m, 2H); 3.73 (s, 3H); 3.79 (s, 3H); 6.82-6.84 (m, 1H); 6.90-6.92 (m, 1H); 6.95-6.99 (m, 1H); 7.75-7.77 (m, 1H); 7.80-7.82 (m, 1H); 8.14 (br s, 1H); 8.41 (s, 1H); HPLC (METHOD [A]): rt 11.49 min (94.5%)

Workup

  1. customThe compound was synthesized
  2. customrt 11.49 min (94.5%)

Sources & evidence

ORD record
ord-cc507460079644b795a251867526e97c
Source dataset
uspto-grants-2015_11
Patent number
US09181233B2

Linked notes

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