Phenoxyacetic Acid → HCID 178420516, compound

HRID 710520Notes

Reaction equation

HRID 710520 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([NH:12][NH2:13])=[O:11])=[CH:9][C:4]=2[NH:3][CH:2]=1.[O:14]([CH2:21][C:22](O)=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[O:14]([CH2:21][C:22]1[O:11][C:10]([C:8]2[CH:7]=[CH:6][C:5]3[NH:1][CH:2]=[N:3][C:4]=3[CH:9]=2)=[N:12][N:13]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 19188Phenoxyacetic AcidHCID 166371191H-benzimidazole-5-carbohydrazide

Product 1

HCID 178420516HCID 178420516, compound

Procedure

The compound was synthesized starting from Benzimidazol-5-carbohydrazide (176 mg, 1 mmol) and Phenoxyacetic acid (153 mg; 1 mmol) as described in method 2 but purified by flash chromatography on silica using a CHCl3/MeOH gradient; yield: 0.049 g (16.8%); MS m/z: 293.2 [M+H]+; 1H-NMR (DMSO d6, 400 MHz): □5.48 (s, 2H); 7.00-7.03 (m, 1H); 7.11-7.13 (m, 2H); 7.32-7.36 (m, 2H); 7.78 (d, 1H, 3J=8.3 Hz); 7.86 (dd, 1H, 4J=1.7 Hz, 3J=8.3 Hz); 8.20 (br s, 1H); 8.40 (s, 1H); 12.82 (br s, 1H); HPLC (METHOD [A]): rt 11.29 min (100%)

Workup

  1. customThe compound was synthesized
  2. custompurified by flash chromatography on silica using a CHCl3/MeOH gradient
  3. customrt 11.29 min (100%)

Sources & evidence

ORD record
ord-61e612684a7843f6888eb6b58f85f23f
Source dataset
uspto-grants-2015_11
Patent number
US09181233B2

Reaction notes

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