Chloroacetyl chloride → HCID 23513422, compound
Reaction equation
C(N(CC)CC)C.[OH:8][C:9]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:10]=1[NH2:11].[Cl:17][CH2:18][C:19](Cl)=[O:20]>O1CCCC1>[Cl:17][CH2:18][C:19]([NH:11][C:10]1[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:9]=1[OH:8])=[O:20]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 26 °C
Procedure
95 ml of triethylamine (0.674 mol) were added to a solution of 83 g of 2-hydroxy-4-methylaniline (0.674 mol) in 2.5 liters of tetrahydrofuran, with stirring and under an inert atmosphere, followed, after 30 minutes, by dropwise addition of a solution of 54 ml of chloroacetyl chloride (0.678 mol) in 60 ml of tetrahydrofuran, while maintaining the temperature at 25-27° C. The reaction medium was stirred at room temperature for 4 hours, filtered through a sinter funnel and the inorganic salts were rinsed with 500 ml of tetrahydrofuran. The combined organic phases were poured into 3 liters of ice-cold water with stirring. The precipitate formed was spin-filtered, washed with twice 600 ml of water and once with pentane, and dried under vacuum to constant weight, to give 99 g of 2-chloro-N-(2-hydroxy-4-methylphenyl)acetamide in the form of a beige-coloured powder, in a yield of 74%.
Workup
- stirringThe reaction medium was stirred at room temperature for 4 hours
- filtrationfiltered through a sinter funnel
- washthe inorganic salts were rinsed with 500 ml of tetrahydrofuran
- additionThe combined organic phases were poured into 3 liters of ice-cold water
- stirringwith stirring
- customThe precipitate formed
- filtrationwas spin-filtered
- washwashed with twice 600 ml of water and once with pentane
- customdried under vacuum to constant weight
Sources & evidence
- ORD record
- ord-ef1c25e2a3244a33b006289dcb19e83b
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06455737B1
Reaction notes
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