Chloroacetyl chloride → 3-[4-(2-Chloroacetylamino)-3-hydroxyphenyl]acrylic acid ethyl ester

HRID 850609Notes

Reaction equation

HRID 850609 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([OH:14])[CH:8]=1)[CH3:2].C([O-])(O)=O.[Na+].[Cl:21][CH2:22][C:23](Cl)=[O:24]>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:15])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:23](=[O:24])[CH2:22][Cl:21])=[C:9]([OH:14])[CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 540473973-(4-Amino-3-hydroxyphenyl)-acrylic acid ethyl ester

Product 1

HCID 541602373-[4-(2-Chloroacetylamino)-3-hydroxyphenyl]acrylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 10-3 (3.38 g, 16.3 mmol) in CHCl3 (80 mL) was added saturated NaHCO3 (50 mL) and it was then chilled to 0° C. A solution of chloroacetyl chloride (1.94 mL, 24.4 mmol) in CHCl3 (30 mL) was added dropwise to the chilled biphase. Upon addition completion, the reaction was stirred at 0° C. for 1 h. The layers were separated and the aqueous layer was extracted twice with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated to give 10-4 which was used without further purification in the next step.

Workup

  1. additionUpon addition completion
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted twice with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto give 10-4 which
  8. customwas used without further purification in the next step

Sources & evidence

ORD record
ord-a24781472ece49839d630c0d219d1c3d
Source dataset
uspto-grants-2000_01
Patent number
US06017926

Reaction notes

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