Phosphorus oxychloride → HCID 178505669, compound

HRID 710533Notes

Reaction equation

HRID 710533 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11](O)=O)[CH:5]=[CH:6][C:7]=1[F:8].[N:14]1[C:18]2[CH:19]=[CH:20][C:21]([C:23]([NH:25][NH2:26])=O)=[CH:22][C:17]=2[NH:16][CH:15]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:36])=CC=1.O=P(Cl)(Cl)Cl>>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[F:8])[CH2:9][CH2:10][C:11]1[S:36][C:23]([C:21]2[CH:20]=[CH:19][C:18]3[NH:14][CH:15]=[N:16][C:17]=3[CH:22]=2)=[N:25][N:26]=1

Participants

5

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 87949Lawesson's reagentHCID 27789943,4-Difluorohydrocinnamic acidHCID 166371191H-benzimidazole-5-carbohydrazide

Product 1

HCID 178505669HCID 178505669, compound

Procedure

The compound was synthesized starting from 3-(3,4-difluorophenyl)propionic acid (186 mg; 1 mmol), benzimidazol-5-carbohydrazide (176 mg; 1 mmol), Lawesson's reagent (606 mg; 1.5 mmol) and POCl3 (0.137 ml; 1.5 mmol) as described in method 3; yield: 0.02 g (5.8%); MS m/z: 343.3 [M+H]+; 1H-NMR (DMSO d6, 400 MHz): δ 3.11 (t, 2H, 3J=7.5 Hz); 3.47 (t, 2H, 3J=7.5 Hz); 6.97-6.99 (m, 1H); 7.32-7.35 (m, 1H); 7.40-7.46 (m, 1H); 7.82 (d, 1H, 3J=8.7 Hz); 7.91 (dd, 1H, 4J=1.7 Hz, 3J=8.7 Hz); 8.22 (d, 1H, 4J=1.7 Hz), 8.87 (s, 1H); HPLC (METHOD [A]): rt 13.09 min (85.7%)

Workup

  1. customThe compound was synthesized
  2. customrt 13.09 min (85.7%)

Sources & evidence

ORD record
ord-12ae1729aed242c384bcf4be1bb03653
Source dataset
uspto-grants-2015_11
Patent number
US09181233B2

Reaction notes

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