Water → 2-(N-[3-chlorobenzyl]isobutyramido)-4-methyloxazole

HRID 26489

Reaction equation

HRID 26489 reaction equation
[C:1]([NH:6][C:7]1[O:8][CH:9]=[C:10]([CH3:12])[N:11]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[Cl:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23]Br.O>CN(C)C=O>[Cl:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][N:6]([C:7]1[O:8][CH:9]=[C:10]([CH3:12])[N:11]=1)[C:1](=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 233485622-iso Butyramido-4-methyloxazole

Product 1

HCID 213236682-(N-[3-chlorobenzyl]isobutyramido)-4-methyloxazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

2-iso Butyramido-4-methyloxazole (11.1 g., 0.066 mol) prepared in a manner similar to that described in Example 20, was dissolved in dry dimethylformamide. Solid potassium carbonate (10.47 g., 0.076 mol) and 3-chlorobenzyl bromide (15.6 g., 0.076 mol) were added and the stirred mixture was heated at 70° C. for 2 hours, cooled and poured into cold water. The solution was extracted with ether and the extract was dried over magnesium sulphate and evaporated. The residue was distilled to give the product, 12.3 g., b.p. 115-120° C./0.08 mm.

Workup

  1. temperaturecooled
  2. extractionThe solution was extracted with ether
  3. dry with materialthe extract was dried over magnesium sulphate
  4. customevaporated
  5. distillationThe residue was distilled
  6. customto give the product, 12.3 g

Sources & evidence

ORD record
ord-67daa2cca30b41ff8b2d549f760e35e1
Source dataset
uspto-grants-1979_04
Patent number
US04150143

Linked notes

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