Phosphorus oxychloride → HCID 178527396, compound

HRID 710540Notes

Reaction equation

HRID 710540 reaction equation
[C:1]1([S:7]([CH2:10][C:11](O)=O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[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>>[C:1]1([S:7]([CH2:10][C:11]2[S:36][C:23]([C:21]3[CH:20]=[CH:19][C:18]4[NH:14][CH:15]=[N:16][C:17]=4[CH:22]=3)=[N:25][N:26]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 59543(phenylsulfonyl)acetic acidHCID 87949Lawesson's reagentHCID 166371191H-benzimidazole-5-carbohydrazide

Product 1

HCID 178527396HCID 178527396, compound

Procedure

The compound was synthesized starting from phenylsulfonylacetic acid (201 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: 0.051 G (14.3%); MS m/z: 357.1 [M+H]+; 1H-NMR (DMSO d6, 400 MHz): δ 5.51 (s, 2H); 7.63-7.67 (m, 2H); 7.75-7.77 (m, 1H); 7.84-7.87 (m, 3H); 7.98 (dd, 1H, 4J=1.7 Hz, 3J=8.3 Hz); 8.30 (d, 1H, 4J=1.7 Hz); 8.95 (s, 1H); HPLC (METHOD [A]): rt 10.49 min (98.3%)

Workup

  1. customThe compound was synthesized
  2. customrt 10.49 min (98.3%)

Sources & evidence

ORD record
ord-49e861ce348546ff853bf084bd8e5822
Source dataset
uspto-grants-2015_11
Patent number
US09181233B2

Reaction notes

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