Phosphorus oxychloride → HCID 178506155, compound

HRID 710529Notes

Reaction equation

HRID 710529 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11](O)=O)=[CH:5][CH:4]=1.[N:16]1[C:20]2[CH:21]=[CH:22][C:23]([C:25]([NH:27][NH2:28])=O)=[CH:24][C:19]=2[NH:18][CH:17]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:38])=CC=1.O=P(Cl)(Cl)Cl>>[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[S:38][C:25]([C:23]3[CH:22]=[CH:21][C:20]4[NH:16][CH:17]=[N:18][C:19]=4[CH:24]=3)=[N:27][N:28]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 87949Lawesson's reagentHCID 35887363-(4-(Trifluoromethyl)phenyl)propionic AcidHCID 166371191H-benzimidazole-5-carbohydrazide

Product 1

HCID 178506155HCID 178506155, compound

Procedure

The compound was synthesized starting from 3-(4-trifluoromethylphenyl)propionic acid (219 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: 0.017 g (4.5%); MS m/z: 375.1 [M+H]+; 1H-NMR (DMSO d6, 400 MHz): δ 3.22 (t, 2H, 3J=7.5 Hz); 3.52 (t, 2H, 3J=7.5 Hz); 7.53-7.55 (m, 2H); 7.65-7.67 (m, 2H); 7.84 (d, 1H, 3J=8.7 Hz); 7.92 (dd, 1H, 4J=1.7 Hz, 3J=8.7 Hz); 8.22-8.23 (m, 1H); 8.93 (s, 1H); HPLC (METHOD [A]): rt 14.82 min (98.3%)

Workup

  1. customThe compound was synthesized
  2. customrt 14.82 min (98.3%)

Sources & evidence

ORD record
ord-cd70888ee9da44a59a078a0d613af905
Source dataset
uspto-grants-2015_11
Patent number
US09181233B2

Reaction notes

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