Chloroacetyl chloride → HCID 23513422, compound

HRID 1741537Notes

Reaction equation

HRID 1741537 reaction equation
O1CCOCC1.[NH2:7][C:8]1[CH:9]=[CH:10][C:11]([CH3:15])=[CH:12][C:13]=1[OH:14].C(=O)([O-])[O-].[Ca+2].[Cl:21][CH2:22][C:23](Cl)=[O:24]>O>[OH:14][C:13]1[CH:12]=[C:11]([CH3:15])[CH:10]=[CH:9][C:8]=1[NH:7][C:23](=[O:24])[CH2:22][Cl:21]

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 10112Calcium CarbonateHCID 312751,4-DioxaneHCID 760822-Amino-5-methylphenol

Product 1

HCID 23513422HCID 23513422, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To 130 ml of dioxane, were added 20.0 g (163 mmol) of 6-amino-m-cresol and 9.2 g (92 mmol) of calcium carbonate, followed by heating to 60° C. To the obtained solution, there was added 22.1 g (196 mmol) of chloroacetyl chloride over 40 minutes and the mixture was further stirred at 60° C. for 2 hours. After cooling, the mixture was poured into 500 ml of water, extracted with 700 ml of ethyl acetate and dried over anhydrous Glauber's salt. After distilling off the solvent under reduced pressure, the obtained greenish brown solid was recrystallized from acetonitrile. Thus 23.5 g (118 mmol) of N-(2-hydroxy-4-methylphenyl)chloroacetamide was obtained as pale green crystals. The yield was 72%.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with 700 ml of ethyl acetate
  3. dry with materialdried over anhydrous Glauber's salt
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe obtained greenish brown solid was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-34621178c7864513a7d12c143f7d0bb7
Source dataset
uspto-grants-1994_08
Patent number
US05334225

Reaction notes

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