Pyridine → N-(5-tert-Butyl-1,2-oxazol-3-yl)-2-chloroacetamide

HRID 1453794Notes

Reaction equation

HRID 1453794 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[C:6]([C:10]1[O:14][N:13]=[C:12]([NH2:15])[CH:11]=1)([CH3:9])([CH3:8])[CH3:7].N1C=CC=CC=1>ClCCl>[C:6]([C:10]1[O:14][N:13]=[C:12]([NH:15][C:3](=[O:4])[CH2:2][Cl:1])[CH:11]=1)([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 1714733-Isoxazolamine, 5-(1,1-dimethylethyl)-

Product 1

HCID 28065541N-(5-tert-Butyl-1,2-oxazol-3-yl)-2-chloroacetamideYield 132.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Chloroacetic acid chloride (0.93 ml; II.42 mmol) is dropped slowly into a stirred solution of 5-t-Butyl-3-amino isoxazole (1.5 g; 7.67 mmol) in pyridine (1.09 ml; 13.49 mmol) and dichloromethane (20 ml), cooled to 0° C. Stirring is continued for 2 h at room temperature. The reaction mixture is diluted with dichloromethane, washed twice with 1N aqueous hydrochloric acid, twice with an aqueous solution of NaHCO3 and with water. The reaction mixture is then dried over Na2SO4, filtered and evaporated to yield 2.2 g (98%) brownish solid of 10.

Workup

  1. washwashed twice with 1N aqueous hydrochloric acid, twice with an aqueous solution of NaHCO3 and with water
  2. dry with materialThe reaction mixture is then dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-8f158e65f616455e926b177b9eb292ca
Source dataset
uspto-grants-2009_01
Patent number
US07476683B2

Reaction notes

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