Chloroacetyl chloride → HCID 15654664, compound

HRID 1655470Notes

Reaction equation

HRID 1655470 reaction equation
[NH2:1][C:2]1[C:3]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]#[N:28])=[CH:17][CH:16]=2)=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(N(CC)CC)C.[Cl:36][CH2:37][C:38](Cl)=O.[OH-].[Na+]>C(Cl)Cl.O>[Cl:36][CH2:37][C:38]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]#[N:28])=[CH:17][CH:16]=2)[C:3]2[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:10][CH:11]=[CH:12][C:2]=2[N:1]=1

Participants

7

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 15654655Ethyl 3-amino-2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)benzoate

Product 1

HCID 15654664HCID 15654664, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled solution of ethyl 3-amino-2-[(2'-cyanobiphenyl-4-yl)methyl]aminobenzoate (1.0 g) and triethylamine (0.3 g) in methylenechloride (10 ml) was added chloroacetyl chloride (0.24 ml) in portions. The mixture was allowed to stir for 13 hours and then evaporated to dryness to give a residue. The residue was washed with H2O, dried and dissolved in EtOH (10 ml). To the solution was added conc-HCl (1 ml) and the solution was refluxed for 6 hours. The reaction solution was evaporated to dryness to give a residue and the residue was dissolved in methylene chloride and water. The solution was made basic with 1N-NaOH and the organic layer was washed with water, dried and evaporated to dryness to give crystals Recrystallization from ethyl acetate-isopropylether gave colorless crystals (0.88 g, 76%) 1H-NMR(200 MHz, CDCl3) δ: 1.21(3H,t), 4.21(2H,q), 4.83(2H,s), 6.02(2H,s), 7.02(2H,d), 7.29- 7.49(5H,m), 7.58-7.79(3H,m), 8.00 (1H,dd).

Workup

  1. customevaporated to dryness
  2. customto give a residue
  3. washThe residue was washed with H2O
  4. customdried
  5. dissolutiondissolved in EtOH (10 ml)
  6. additionTo the solution was added conc-HCl (1 ml)
  7. temperaturethe solution was refluxed for 6 hours
  8. customThe reaction solution was evaporated to dryness
  9. customto give a residue
  10. washthe organic layer was washed with water
  11. customdried
  12. customevaporated to dryness
  13. customto give
  14. customcrystals Recrystallization from ethyl acetate-isopropylether

Sources & evidence

ORD record
ord-93d91c382b58497b852805afc91b7381
Source dataset
uspto-grants-1993_10
Patent number
US05250554

Reaction notes

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