Dicyclohexylcarbodiimide → HCID 178490063, compound

HRID 710534Notes

Reaction equation

HRID 710534 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11](O)=O)[CH:6]=[CH:7][CH:8]=1.C1CCC(N=C=NC2CCCCC2)CC1.[N:29]1[C:33]2[CH:34]=[CH:35][C:36]([C:38]([NH:40][NH2:41])=O)=[CH:37][C:32]=2[NH:31][CH:30]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:51])=CC=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[CH2:9][CH2:10][C:11]1[S:51][C:38]([C:36]2[CH:35]=[CH:34][C:33]3[NH:29][CH:30]=[N:31][C:32]=3[CH:37]=2)=[N:40][N:41]=1

Participants

5

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 663363-(m-Methoxyphenyl)propionic acidHCID 87949Lawesson's reagentHCID 166371191H-benzimidazole-5-carbohydrazide

Product 1

HCID 178490063HCID 178490063, compound

Procedure

The compound was synthesized starting from 3-(3-methoxyphenyl)propionic acid (181 mg; 1 mmol), DCC (206 mg; 1 mmol), benzimidazol-5-carbohydrazide (176 mg; 1 mmol) and Lawesson's reagent (606 mg; 1.5 mmol) as described in method 2; yield: 0.019 g (5.7%); MS m/z: 337.3 [M+H]+; 1H-NMR (DMSO d6, 400 MHz): δ 3.08 (t, 2H, 3J=7.5 Hz); 3.46 (t, 2H, 3J=7.5 Hz); 3.72 (s, 3H); 6.76-6.78 (m, 1H); 6.85-6.88 (m, 2H); 7.20 (t, 1H, 3J=7.9 Hz); 7.81 (d, 1H, 3J=8.7 Hz); 7.89 (dd, 1H, 4J=1.7 Hz, 3J=8.7 Hz); 8.20 (d, 1H, 4J=1.7 Hz); 8.83 (s, 1H); HPLC (METHOD [A]): rt 12.24 min (95.9%)

Workup

  1. customThe compound was synthesized
  2. customrt 12.24 min (95.9%)

Sources & evidence

ORD record
ord-2a67e64e77b64365b55748f17790d568
Source dataset
uspto-grants-2015_11
Patent number
US09181233B2

Reaction notes

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