Phenoxyacetic Acid → HCID 178420517, compound

HRID 710538Notes

Reaction equation

HRID 710538 reaction equation
[O:1]([CH2:8][C:9](O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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>>[O:1]([CH2:8][C:9]1[S:34][C:21]([C:19]2[CH:18]=[CH:17][C:16]3[NH:12][CH:13]=[N:14][C:15]=3[CH:20]=2)=[N:23][N:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 19188Phenoxyacetic AcidHCID 24813Phosphorus oxychlorideHCID 87949Lawesson's reagentHCID 166371191H-benzimidazole-5-carbohydrazide

Product 1

HCID 178420517HCID 178420517, compound

Procedure

The compound was synthesized starting from phenoxyacetic acid (153 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: 0.031 g (10.1%); MS m/z: 309.0 [M+H]+; 1H-NMR (DMSO d6, 400 MHz): δ 5.64 (s, 2H); 6.99-7.03 (m, 1H); 7.09-7.12 (m, 2H); 7.32-7.36 (m, 2H); 7.84 (d, 1H, 3J=8.3 Hz); 7.98 (dd, 1H, 4J=1.7 Hz, 3J=8.3 Hz); 8.31 (d, 1H, 4J=1.7 Hz); 8.90 (s, 1H); HPLC (METHOD [A]): rt 12.07 min (95.9%)

Workup

  1. customThe compound was synthesized
  2. customrt 12.07 min (95.9%)

Sources & evidence

ORD record
ord-3fc85561f6d447c8ac44b363e4852e4f
Source dataset
uspto-grants-2015_11
Patent number
US09181233B2

Reaction notes

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