Phenylacetyl chloride → HCID 178420211, compound

HRID 710508Notes

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.[C:14]1([CH2:20][C:21](Cl)=O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O=P(Cl)(Cl)Cl>>[CH2:20]([C:21]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)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Reactant 3

HCID 7679Phenylacetyl chloride

HCID 24813Phosphorus oxychloride

HCID 166371191H-benzimidazole-5-carbohydrazide

Product 1

HCID 178420211HCID 178420211, compound

Procedure

The compound was synthesized starting from benzimidazol-5-carbohydrazide (176 mg, 1 mmol), TEA (0.153 ml; 1.1 mmol), phenylacetylchloride (170 mg, 0.145 ml, 1.1 mmol) and POCl3 (0.5 ml; 5.5 mmol) as described in method 1; yield: 0.026 mg (9.4%); MS m/z: 277.4 [M+H]+; 1H-NMR (DMSO d6, 400 MHz): δ 4.34 (s, 2H); 7.25-7.28 (m, 1H); 7.29-7.38 (m, 4H); 7.83 (d, 1H, 3J=8.7 Hz); 7.91 (dd, 1H, 4J=1.7 Hz, 3J=8.7 Hz); 8.19-8.20 (m, 1H); 8.85 (s, 1H); HPLC (METHOD [A]): rt 11.17 min (100%)

Workup

customThe compound was synthesized
customrt 11.17 min (100%)

Sources & evidence

ORD record: ord-b5bb7f4eab5e4f71bdf8444438fe2fe8
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181233B2

Reaction notes

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