Phosphorus oxychloride → HCID 178420565, compound

HRID 710539Notes

Reaction equation

HRID 710539 reaction equation
[C:1]1([S:7][CH2:8][C:9](O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:12]1[C:16]2[CH:17]=[CH:18][C:19]([C:21]([NH:23][NH2:24])=O)=[CH:20][C:15]=2[NH:14][CH:13]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:34])=CC=1.O=P(Cl)(Cl)Cl>>[C:1]1([S:7][CH2:8][C:9]2[S:34][C:21]([C:19]3[CH:18]=[CH:17][C:16]4[NH:12][CH:13]=[N:14][C:15]=4[CH:20]=3)=[N:23][N:24]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 59541(Phenylthio)acetic acidHCID 87949Lawesson's reagentHCID 166371191H-benzimidazole-5-carbohydrazide

Product 1

HCID 178420565HCID 178420565, compound

Procedure

The compound was synthesized starting from (phenylthio)acetic acid (169 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: 0.019 g (5.9%); MS m/z: 325.7 [M+H]+; 1H-NMR (DMSO d6, 400 MHz): δ 4.77 (s, 2H); 7.21-7.25 (m, 1H); 7.31-7.35 (m, 2H); 7.43-7.45 (m, 2H); 7.79 (d, 1H, 3J=8.3 Hz); 7.89 (dd, 1H, 4J=1.7 Hz, 3J=8.3 Hz); 8.21 (br s, 1H); 8.83 (s, 1H); HPLC (METHOD [A]): rt 12.30 min (95.2%)

Workup

  1. customThe compound was synthesized
  2. customrt 12.30 min (95.2%)

Sources & evidence

ORD record
ord-e8d48032607c447c9705b2936283194b
Source dataset
uspto-grants-2015_11
Patent number
US09181233B2

Reaction notes

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