Chloroacetyl chloride → HCID 70127462, compound

HRID 651380Notes

Reaction equation

HRID 651380 reaction equation
[CH2:1]([O:8][C:9](=[O:20])[NH:10][C:11]1[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:12]=1[NH2:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:28][CH2:29][C:30](Cl)=[O:31]>C1COCC1>[CH2:1]([O:8][C:9](=[O:20])[NH:10][C:11]1[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:12]=1[NH:19][C:30](=[O:31])[CH2:29][Cl:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 70127080HCID 70127080, compound

Product 1

HCID 70127462HCID 70127462, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cool solution of (2-amino-6-methoxyphenyl)carbamic acid benzyl ester (9.5 g; 34.9 mmol) and triethylamine (5.8 ml; 42 mmol) in anhydrous THF (90 ml), chloroacetylchloride (3.3 ml; 42 mmol) was added dropwise. The mixture was stirred at 0° C. for 2 hours, the solvent was evaporated and the residue was dissolved in ethyl acetate. The organic layer was washed with 10% aqueous HCl and diluted aqueous Na2 CO3 then it was dried and evaporated. The crude residue was crystallized with n-hexane to give the title compound as a white solid. 10.8 g.

Workup

  1. customthe solvent was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe organic layer was washed with 10% aqueous HCl and diluted aqueous Na2 CO3
  4. customit was dried
  5. customevaporated
  6. customThe crude residue was crystallized with n-hexane

Sources & evidence

ORD record
ord-2efb21df2f9e4eceaf7150605d1b1264
Source dataset
uspto-grants-2001_08
Patent number
US06281218B1

Reaction notes

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