3-Amino-5-methylisoxazole → 4-Hydroxy-3-(5-methyl-3-isoxazolylcarbamoyl)-2H-1,2-benzothiazine 1,1-Dioxide

HRID 1703724Notes

Reaction equation

HRID 1703724 reaction equation
[C:1]([C:6]1[N:7](C)[S:8](=[O:18])(=[O:17])[C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[C:11]=1[OH:12])([O:3]CC)=O.[NH2:20][C:21]1[CH:25]=[C:24]([CH3:26])[O:23][N:22]=1>C1(C)C(C)=CC=CC=1>[OH:12][C:11]1[C:10]2[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=2[S:8](=[O:17])(=[O:18])[NH:7][C:6]=1[C:1](=[O:3])[NH:20][C:21]1[CH:25]=[C:24]([CH3:26])[O:23][N:22]=1

Participants

4

Reactant 2

HCID 661723-Amino-5-methylisoxazoleHCID 546793484-Hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid ethylester 1,1-dioxide

Product 1

HCID 547081504-Hydroxy-3-(5-methyl-3-isoxazolylcarbamoyl)-2H-1,2-benzothiazine 1,1-Dioxide

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 15.3 g. (0.06 mole) of 3-carbethoxy-4-hydroxy-2-methyl-2H-1,2-benzothiazine 1,1-dioxide, 5.9 g. (0.06 mole) of 3-amino-5-methylisoxazole, and 800 ml. of xylene was refluxed for 24 hr. in a Soxhlet apparatus, the thimble of which contained 20 g. of Linde type 4A molecular sieve. The mixture was cooled to 25° and the resulting precipitate was collected and washed with ether to give 11.5 g. of crude product, m.p. 242-248° dec. Recrystallization from 300 ml. of 1,4-dioxan gave 11.2 g. of crystalline product, m.p. 254-257° dec.

Workup

  1. additionA mixture of 15.3 g
  2. temperatureThe mixture was cooled to 25°
  3. customthe resulting precipitate was collected
  4. washwashed with ether
  5. customto give 11.5 g
  6. customRecrystallization from 300 ml
  7. customof 1,4-dioxan gave 11.2 g

Sources & evidence

ORD record
ord-7e3d6e9d37a7405eaa44d78ebfefe4a2
Source dataset
uspto-grants-1978_11
Patent number
USRE029836

Reaction notes

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