Triethylamine → 2-(4-Chlorobutyramido)-4-methyloxazole

HRID 1112385Notes

Reaction equation

HRID 1112385 reaction equation
[NH2:1][C:2]1[O:3][CH:4]=[C:5]([CH3:7])[N:6]=1.C(N(CC)CC)C.[Cl:15][CH2:16][CH2:17][CH2:18][C:19](Cl)=[O:20]>C1C=CC=CC=1>[Cl:15][CH2:16][CH2:17][CH2:18][C:19]([NH:1][C:2]1[O:3][CH:4]=[C:5]([CH3:7])[N:6]=1)=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 783704-Chlorobutyryl chlorideHCID 5358244-Methyloxazol-2-amine

Product 1

HCID 213236452-(4-Chlorobutyramido)-4-methyloxazoleYield 23.92%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

2-Amino-4-methyloxazole (5.0 g., 0.0509 mol) was dissolved in dry benzene (100 mls.) and triethylamine (5.70 g., 0.0563 mol) was added. The mixture was stirred vigorously at room temperature and 4-chlorobutyrylchloride (7.88 g., 0.0558 mol) in dry benzene (50 mls.) was added rapidly. After the addition the mixture was heated under reflux for 2 hours. The mixture was then cooled and fltered. The filtrate was placed in a separating funnel and washed successively with water (1 × 100 mls.), 10% Na2CO3 (2 × 100 mls.) and water (3 × 100 mls.). The organic layer was driec over magnesium sulphate and evaporated under vacuum. The product was recrystallised from ethyl acetate/hexane. Wt. = 2.47 g. m.p. 98° C. (Yield = 23.92%).

Workup

  1. additionAfter the addition the mixture
  2. temperaturewas heated
  3. temperatureunder reflux for 2 hours
  4. temperatureThe mixture was then cooled
  5. customThe filtrate was placed in a separating funnel
  6. washwashed successively with water (1 × 100 mls.), 10% Na2CO3 (2 × 100 mls.) and water (3 × 100 mls.)
  7. customevaporated under vacuum
  8. customThe product was recrystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-35832c43f16d46d1ab02c407a8a7d7eb
Source dataset
uspto-grants-1978_10
Patent number
US04122183

Reaction notes

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