3-Isoxazolamine → 4-Hydroxy-3-(3-isoxazolylcarbamoyl)-2-methyl-2H-1,2-benzothiazine 1,1-Dioxide

HRID 1703723Notes

Reaction equation

HRID 1703723 reaction equation
[C:1]([C:6]1[N:7]([CH3:19])[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]=[CH:24][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])[N:7]([CH3:19])[C:6]=1[C:1](=[O:3])[NH:20][C:21]1[CH:25]=[CH:24][O:23][N:22]=1

Participants

4

Reactant 2

HCID 18102163-IsoxazolamineHCID 546793484-Hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid ethylester 1,1-dioxide

Product 1

HCID 547247964-Hydroxy-3-(3-isoxazolylcarbamoyl)-2-methyl-2H-1,2-benzothiazine 1,1-Dioxide

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 4.15 g. (0.0155 mole) of 3-carbethoxy-4-hydroxy-2-methyl-2H-1,2-benzothiazine 1,1-dioxide, 1.3 g. (0.0155 mole) of 3-aminoisoxazole, and 500 ml. of xylene was refluxed for 24 hr. in a Soxhlet apparatus, the thimble of which contained 10 g. of Linde 4A molecular sieve. The mixture was cooled to 25° and the resulting crystalline precipitate was collected and washed with ether to give 3.2 g. of product, m.p. 235-240° dec. Recrystallization from 175 ml. of ethyl acetate gave 1.6 g. of material, m.p. 237-240° dec.

Workup

  1. additionA mixture of 4.15 g
  2. temperatureThe mixture was cooled to 25°
  3. customthe resulting crystalline precipitate was collected
  4. washwashed with ether
  5. customto give 3.2 g
  6. customRecrystallization from 175 ml
  7. customof ethyl acetate gave 1.6 g

Sources & evidence

ORD record
ord-48836a517bfc443290c6188c109e3605
Source dataset
uspto-grants-1978_11
Patent number
USRE029836

Reaction notes

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