Ethyl Acetate → HCID 25235545, compound

HRID 1360754Notes

Reaction equation

HRID 1360754 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[NH:10][C:11]2[CH:17]=[C:16]([C:18]([NH:20][NH2:21])=[O:19])[CH:15]=[CH:14][C:12]=2[N:13]=1.[Cl:22][C:23]1[CH:24]=[C:25]([N:29]=[C:30]=S)[CH:26]=[CH:27][CH:28]=1.CCN=C=NCCCN(C)C.CCOC(C)=O>CN(C=O)C>[Cl:22][C:23]1[CH:24]=[C:25]([NH:29][C:30]2[O:19][C:18]([C:16]3[CH:15]=[CH:14][C:12]4[N:13]=[C:9]([C:3]5[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=5[Cl:1])[NH:10][C:11]=4[CH:17]=3)=[N:20][N:21]=2)[CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 754493-Chlorophenyl isothiocyanateHCID 577865852-(2,6-Dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide

Product 1

HCID 25235545HCID 25235545, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
4 °C

Procedure

To a solution of 2-(2,6-dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide (150 mg, 0.466 mmol) in DMF (3 mL) add 3-chloro phenyl isothiocyanate (69 uL, 0.512 mmol) and stir for 1.75 hr. Add EDCI (179 mg, 0.932 mmol) and heat to 80° C. for 30 min. Allow to stir at room temp overnight. Dilute the reaction with EtOAc (50 mL) and extract with water (10 mL) and 1 N NaOH (10 mL). Dry the organic phase over Na2SO4 and evaporate the solvent. Combine the aqueous phases, chill to 4° C., and filter. Combine the solids and suspend them in boiling toluene/EtOAc. Cool the suspension to 4° C. and filter. Wash the solid with Et2O. Dry to afford the title compound as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 7.07 (ddd, J=7.96, 2.02, 0.76 Hz, 1H) 7.40 (t, J=8.15 Hz, 1H) 7.50-7.55 (m, 1H) 7.62-7.67 (m, 1H) 7.70 (s, 1H) 7.72 (d, J=2.02 Hz, 1H) 7.75-7.91 (m, 3H) 8.11 (br. s., 1H) 10.99 (br. s., 1H) 13.28 (br. s., 1H); MS m/z=457.9 (M+1).

Workup

  1. stirringto stir at room temp overnight
  2. additionDilute
  3. extractionextract with water (10 mL) and 1 N NaOH (10 mL)
  4. dry with materialDry the organic phase over Na2SO4
  5. customevaporate the solvent
  6. filtrationfilter
  7. temperatureCool the suspension to 4° C.
  8. filtrationfilter
  9. washWash the solid with Et2O
  10. customDry

Sources & evidence

ORD record
ord-5fd785aa1da041e892c6be704bfd6f5f
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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