3-Amino-5-methylisoxazole → HCID 54704474, compound

HRID 2163440Notes

Reaction equation

HRID 2163440 reaction equation
[OH:1][C:2]1[C:3]2[CH:16]=[CH:15][S:14][C:4]=2[S:5](=[O:13])(=[O:12])[CH2:6][C:7]=1[C:8]([O:10]C)=O.[NH2:17][C:18]1[CH:22]=[C:21]([CH3:23])[O:20][N:19]=1>C1(C)C(C)=CC=CC=1>[OH:1][C:2]1[C:3]2[CH:16]=[CH:15][S:14][C:4]=2[S:5](=[O:13])(=[O:12])[CH2:6][C:7]=1[C:8]([NH:17][C:18]1[CH:22]=[C:21]([CH3:23])[O:20][N:19]=1)=[O:10]

Participants

4

Reactant 2

HCID 661723-Amino-5-methylisoxazoleHCID 54704473HCID 54704473, compound

Product 1

HCID 54704474HCID 54704474, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of methyl 4-hydroxy-6H-thieno[2,3-b]thiopyran-5-carboxylate 7,7-dioxide (3.1 g, 0.012 mole), 3-amino-5-methylisoxazole (1.5 g, 0.015 mole) and xylene (120 ml) is refluxed for 1.5 hrs. in a Soxhlet apparatus, the thimble of which contains 15 g of Linde type 4A molecular sieve. The mixture is cooled to 5° C. in an ice-bath, and the resulting crystalline precipitate is collected. The filtrate is refluxed for two additional hours and then cooled to give a second crop. The two fractions are combined and recrystallized from CH2Cl2 --CHCl3 mixture to give a off-white crystalline solid (2.2 g, 56%), m.p. 209-210° C.

Workup

  1. temperatureis refluxed for 1.5 hrs
  2. customthe resulting crystalline precipitate is collected
  3. temperatureThe filtrate is refluxed for two additional hours
  4. temperaturecooled
  5. customto give a second crop
  6. customrecrystallized from CH2Cl2

Sources & evidence

ORD record
ord-4726d4fb8603403ea9f7bd55fea5bb52
Source dataset
uspto-grants-1979_01
Patent number
US04134897

Reaction notes

Loading…