Phosphorus oxychloride → HCID 178506166, compound

HRID 710531Notes

Reaction equation

HRID 710531 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[CH2:13][CH2:14][C:15](O)=O.[N:20]1[C:24]2[CH:25]=[CH:26][C:27]([C:29]([NH:31][NH2:32])=O)=[CH:28][C:23]=2[NH:22][CH:21]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:42])=CC=1.O=P(Cl)(Cl)Cl>>[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[CH2:13][CH2:14][C:15]1[S:42][C:29]([C:27]2[CH:26]=[CH:25][C:24]3[NH:20][CH:21]=[N:22][C:23]=3[CH:28]=2)=[N:31][N:32]=1

Participants

5

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 87949Lawesson's reagentHCID 44459752,5-Bis(trifluoromethyl)hydrocinnamic acidHCID 166371191H-benzimidazole-5-carbohydrazide

Product 1

HCID 178506166HCID 178506166, compound

Procedure

The compound was synthesized starting from 3-(2,5-bis(trifluoromethyl)phenyl)propionic acid (287 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: 0.013 g (2.9%); MS m/z: 443.4 [M+H]+; 1H-NMR (DMSO d6, 400 MHz): δ 3.36-3.40 (m, 2H); 3.51-3.55 (m, 2H); 7.82-7.85 (m, 2H); 7.92 (dd, 1H, 4J=1.7 Hz, 3J=8.3 Hz); 7.97 (d, 1H, 3J=8.3 Hz); 8.06 (br s, 1H); 8.23-8.24 (m, 1H); 8.88 (s, 1H); HPLC (METHOD [A]): rt 16.42 min (96.7%)

Workup

  1. customThe compound was synthesized
  2. customrt 16.42 min (96.7%)

Sources & evidence

ORD record
ord-fa26152109ce4cf2b954414af5f29b7a
Source dataset
uspto-grants-2015_11
Patent number
US09181233B2

Reaction notes

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