Sodium Carbonate → HCID 13341588, compound

HRID 2397788Notes

Reaction equation

HRID 2397788 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:3]=1[C:4](=[N:11][CH2:12][CH2:13][OH:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.ClC(Cl)(Cl)C([NH:24][CH2:25][C:26](O)=[O:27])=O.C1(N=C=NC2CCCCC2)CCCCC1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.CO.O1CCCC1.O>[NH2:24][CH2:25][C:26]([NH:1][C:2]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:3]=1[C:4](=[N:11][CH2:12][CH2:13][OH:14])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:27]

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 10868DicyclohexylcarbodiimideHCID 247510N-(2,2,2-Trichloro-1-hydroxyethylidene)glycineHCID 21436555HCID 21436555, compound

Product 1

HCID 13341588HCID 13341588, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.2g of 2-(2-amino-5-bromo-α-phenylbenzylideneamino)ethanol and 2.6g of trichloroacetylglycine in 50ml of dichloromethane is added 2.5g of N,N'-dicyclohexylcarbodiimide at 0° C., the temperature of the mixture is then raised gradually to room temperature and stirring is continued for 3 hours. After completion of the reaction, the precipitates formed in the reaction mixture is removed by filtration, and the solvent is evaporated from the filtrate to give 4.3g of a crystalline substance melting at 175°-176° C. The crystals are dissolved in a mixture of 80ml of methanol and 80ml of tetrahydrofuran, a solution of 4.0g of sodium carbonate in 80ml of water is added to this solution, and the mixture is stirred at room temperature overnight. After completion of the reaction, the solvent is evaporated from the reaction mixture, the residue extracted with dichloromethane, the extract washed with water, dried over anhydrous sodium sulfate, and the solvent is removed by distillation to give the desired product, which is recrystallized from ethyl acetate affording 0.96g of the desired product melting at 153°-154° C.

Workup

  1. customAfter completion of the reaction
  2. customthe precipitates formed in the reaction mixture
  3. customis removed by filtration
  4. customthe solvent is evaporated from the filtrate
  5. customto give 4.3g of a crystalline substance melting at 175°-176° C
  6. stirringthe mixture is stirred at room temperature overnight
  7. customAfter completion of the reaction
  8. customthe solvent is evaporated from the reaction mixture
  9. extractionthe residue extracted with dichloromethane
  10. washthe extract washed with water
  11. dry with materialdried over anhydrous sodium sulfate
  12. customthe solvent is removed by distillation

Sources & evidence

ORD record
ord-106cc7b1ef2a40cab0cd19deb989d651
Source dataset
uspto-grants-1977_05
Patent number
US04022832

Reaction notes

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