Hydrochloric Acid → HCID 86685372, compound

HRID 570712Notes

Reaction equation

HRID 570712 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]([F:15])([F:14])[F:13])=[CH:6][CH:5]=1)=[C:2]=[S:3].[H-].[Na+].[NH2:18]/[C:19](/[N:26]([CH2:38][C:39]1[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][C:40]=1[O:47][CH3:48])[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:29]=1[O:36][CH3:37])=[CH:20]\[C:21](OCC)=[O:22].Cl>CN(C)C=O>[CH3:48][O:47][C:40]1[CH:41]=[C:42]([O:45][CH3:46])[CH:43]=[CH:44][C:39]=1[CH2:38][N:26]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:29]=1[O:36][CH3:37])[C:19]1[NH:18][C:2](=[S:3])[N:1]([C:4]2[CH:5]=[CH:6][C:7]([O:10][CH2:11][C:12]([F:13])([F:15])[F:14])=[CH:8][CH:9]=2)[C:21](=[O:22])[CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 866436111-Isothiocyanato-4-(2,2,2-trifluoroethoxy)benzeneHCID 86685371ethyl (2E)-3-amino-3-[bis(2,4-dimethoxybenzyl)amino]prop-2-enoate

Product 1

HCID 86685372HCID 86685372, compoundYield 26.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-isothiocyanato-4-(2,2,2-trifluoroethoxy)benzene (3.96 g) in N,N-dimethylformamide (120 mL) was added sodium hydride (60% in oil, 0.68 g) under ice-cooling. The reaction mixture was stirred for 5 min under ice-cooling, ethyl (2E)-3-amino-3-[bis(2,4-dimethoxybenzyl)amino]prop-2-enoate (7.3 g) was added thereto, and the mixture was stirred for 30 min under ice-cooling. To the reaction mixture was added 1M hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was dissolved in ethanol (120 mL), sodium ethoxide (20% ethanol solution, 14.5 mL) was added thereto, and the mixture was stirred for 1 hr. To the reaction mixture was added 1M hydrochloric acid, and the precipitated solid was collected by filtration to give the title compound (2.8 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred for 30 min under ice-
  4. temperaturecooling
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. dissolutionThe residue was dissolved in ethanol (120 mL)
  10. additionsodium ethoxide (20% ethanol solution, 14.5 mL) was added
  11. stirringthe mixture was stirred for 1 hr
  12. additionTo the reaction mixture was added 1M hydrochloric acid
  13. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-49ea6ed81c804d2fbc89dd68dcead293
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

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