Ethyl Acetate → HCID 25235947, compound

HRID 1360750Notes

Reaction equation

HRID 1360750 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.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([N:30]=[C:31]=S)[CH:27]=[CH:28][CH:29]=1.CCN=C=NCCCN(C)C.CCOC(C)=O>CN(C=O)C>[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]3[O:19][C:31]([NH:30][C:26]4[CH:27]=[CH:28][CH:29]=[C:24]([O:23][CH3:22])[CH:25]=4)=[N:21][N:20]=3)[CH:15]=[CH:14][C:12]=2[N:13]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 1378323-Methoxyphenyl isothiocyanateHCID 577865852-(2,6-Dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide

Product 1

HCID 25235947HCID 25235947, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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-methoxy phenyl isothiocyanate (69 uL, 0.512 mmol) and stir for 1.5 hr. Add EDCI (179 mg, 0.932 mmol) and heat to 80° C. for 50 min. Upon cooling to room temp, dilute the reaction with EtOAc (75 mL) and extract with water (15 mL). Evaporate the organic phase and suspend the solid in 1 N NaOH. Collect the solid wash with water and Et2O, Suspend the solid in boiling toluene/EtOAc. Cool the suspension to 4° C. and filter. Wash the solid with Et2O. Again suspend the solid in 1 N NaOH and stir for 1 hr. Collect the solid and wash with water and Et2O. Dry to afford the title compound: 1H NMR (400 MHz, DMSO-d6) δ ppm 3.78 (s, 3H) 6.61 (dd, J=8.15, 1.83 Hz, 1H) 7.14-7.19 (m, 1H) 7.28 (t, J=8.15 Hz, 1H) 7.34 (t, J=2.15 Hz, 1H) 7.64 (dd, J=9.35, 6.69 Hz, 1H) 7.70 (s, 1H) 7.84 (br. s., 2H) 7.72 (d, J=1.89 Hz, 1H) 8.11 (br. s., 1H) 10.67 (br. s., 1H) 13.29 (br. s., 1H); MS m/z=452.1 (M+1).

Workup

  1. additiondilute
  2. extractionextract with water (15 mL)
  3. customEvaporate the organic phase
  4. customCollect the solid
  5. washwash with water and Et2O
  6. temperatureCool the suspension to 4° C.
  7. filtrationfilter
  8. washWash the solid with Et2O
  9. stirringstir for 1 hr
  10. customCollect the solid
  11. washwash with water and Et2O
  12. customDry

Sources & evidence

ORD record
ord-3a33bb6bf42e4b6a893fde9641c9ee5d
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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