Water → Isamoxole

HRID 1112383Notes

Reaction equation

HRID 1112383 reaction equation
[CH2:1]([NH:5][C:6]1[O:7][CH:8]=[C:9]([CH3:11])[N:10]=1)[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.[C:19](Cl)(=[O:23])[CH:20]([CH3:22])[CH3:21].O>C1C=CC=CC=1>[CH2:1]([N:5]([C:6]1[O:7][CH:8]=[C:9]([CH3:11])[N:10]=1)[C:19](=[O:23])[CH:20]([CH3:22])[CH3:21])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 122952262-Oxazolamine, N-butyl-4-methyl-

Product 1

HCID 42118IsamoxoleYield 80%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-(N-butylamino)-4-methyloxazole (106.7 g., 0.69 m.) and triethylamine (110 g., 0.77 m.) were stirred together in dry benzene (1500 c.c.) during the addition of isobutyryl chloride (81.0 g., 0.76 m.). The mixture was stirred at room temperature for 15 hours and then water (1 liter) was added. After stirring for a further hour the organic phase was separated, and the aqueous phase extracted twice in ether. The combined extract was washed successively with 2N hydrochloric acid (2 × 500 c.c.), 10% sodium carbonate solution (2 × 500 c.c.), and saturated brine (2 × 500 c.c.). Evaporation of the dried organic phase gave an oil, which was distilled to give 2-(N-butyl isobutyramido)-4-methyloxazole, (118 g., 80%), b.p. 75°-76° C/0.15 mm., which existed as an oil at room temperature but crystallised on cooling to 0° C.

Workup

  1. stirringAfter stirring for a further hour the organic phase
  2. customwas separated
  3. extractionthe aqueous phase extracted twice in ether
  4. extractionThe combined extract
  5. washwas washed successively with 2N hydrochloric acid (2 × 500 c.c.), 10% sodium carbonate solution (2 × 500 c.c.), and saturated brine (2 × 500 c.c.)
  6. customEvaporation of the dried organic phase
  7. customgave an oil, which
  8. distillationwas distilled

Sources & evidence

ORD record
ord-70eda08a00a04820bb814dca19d369c3
Source dataset
uspto-grants-1978_10
Patent number
US04122183

Reaction notes

Loading…