Phosphorus oxychloride → HCID 178505670, compound

HRID 710532Notes

Reaction equation

HRID 710532 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11](O)=O.[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:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[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 49863953-(2,4-difluorophenyl)propanoic AcidHCID 166371191H-benzimidazole-5-carbohydrazide

Product 1

HCID 178505670HCID 178505670, compound

Procedure

The compound was synthesized starting from 3-(2,4-difluorophenyl)propionic acid (187 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: 0.009 g (2.6%); MS m/z: 342.2 [M+H]+; 1H-NMR (DMSO d6, 400 MHz): δ 3.12 (t, 2H, 3J=7.5 Hz); 3.44 (t, 2H, 3J=7.5 Hz); 7.02-7.05 (m, 1H); 7.17-7.22 (m, 1H); 7.40-7.46 (m, 1H); 7.79 (d, 1H, 3J=8.7 Hz); 7.87 (dd, 1H, 4J=1.7 Hz, 3J=8.7 Hz); 8.19 (d, 1H, 4J=1.7 Hz); 8.72 (s, 1H); HPLC (METHOD [A]): rt 12.69 min (85.5%)

Workup

  1. customThe compound was synthesized
  2. customrt 12.69 min (85.5%)

Sources & evidence

ORD record
ord-1bc77ff341e544afa08905767469af26
Source dataset
uspto-grants-2015_11
Patent number
US09181233B2

Reaction notes

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