Isamoxole → N-Butyl-N-(5-hydroxy-4-methyl-1,3-oxazol-2-YL)-2-methylpropanamide

HRID 26490

Reaction equation

HRID 26490 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([N:7]([CH2:13][CH2:14][CH2:15][CH3:16])[C:8](=[O:12])[CH:9]([CH3:11])[CH3:10])[O:5][CH:6]=1.ClC1C=CC=C(C(OO)=[O:25])C=1>C(Cl)Cl>[OH:25][C:6]1[O:5][C:4]([N:7]([CH2:13][CH2:14][CH2:15][CH3:16])[C:8](=[O:12])[CH:9]([CH3:11])[CH3:10])=[N:3][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 42118IsamoxoleHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 21323624N-Butyl-N-(5-hydroxy-4-methyl-1,3-oxazol-2-YL)-2-methylpropanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-methyl-2(N-butylisobutyramido)oxazole (15 g., 0.067 m.) in dry methylene chloride (100 c.c.) was cooled to 0° C. during the addition of m-chloroperbenzoic acid (16 g., 0.023 m.) over 1 hour. The mixture was then stirred at room temperature for 40 hours. The precipitated m-chlorobenzoic acid was then filtered off and the filtrate evaporated to dryness. The residue was taken in ether (100 c.c.) and stirred with 5% aqueous sodium sulphite solution for1 hour. The organic phase was then separated and washed successively with aqueous sodium carbonate (×2) and water, and then dried and evaporated to give a brown oil, 13.9 g.

Workup

  1. filtrationThe precipitated m-chlorobenzoic acid was then filtered off
  2. customthe filtrate evaporated to dryness
  3. stirringstirred with 5% aqueous sodium sulphite solution for1 hour
  4. customThe organic phase was then separated
  5. washwashed successively with aqueous sodium carbonate (×2) and water
  6. customdried
  7. customevaporated
  8. customto give a brown oil, 13.9 g

Sources & evidence

ORD record
ord-be4b426169c842b9afac9cb2fe8a2b09
Source dataset
uspto-grants-1979_04
Patent number
US04150143

Linked notes

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