HCID 13371034, compound → HCID 70410313, compound

HRID 1380408Notes

Reaction equation

HRID 1380408 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[O:8][N:7]=[C:6]([NH2:9])[CH:5]=1.[OH:10][C:11]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[S:14](=[O:22])(=[O:21])[N:13]([CH3:23])[C:12]=1[C:24](OC)=[O:25]>C1(C)C(C)=CC=CC=1>[OH:10][C:11]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[S:14](=[O:22])(=[O:21])[N:13]([CH3:23])[C:12]=1[C:24]([NH:9][C:6]1[CH:5]=[C:4]([CH2:3][O:2][CH3:1])[O:8][N:7]=1)=[O:25]

Participants

4

Reactant 2

HCID 13371034HCID 13371034, compoundHCID 54676532methyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Product 1

HCID 70410313HCID 70410313, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 0.52 g (4 mmole) of 5-(methoxymethyl)-3-isoxazolamine, 1.08 g (4 mmole) of methyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide, and 100 ml of xylene is heated at reflux for six hours in a soxhlet apparatus, the thimble of which contains 20 g of Linde type 4A molecular sieve. The reaction mixture is filtered to clarify it and is allowed to stand at room temperature overnight when the product crystallizes out. The product is filtered, washed with methanol-ether mixture, and then recrystallized from methanol to give 0.326 g of white crystals, mp 218°-223° C. dec.

Workup

  1. temperatureis heated
  2. temperatureat reflux for six hours in a soxhlet apparatus
  3. filtrationThe reaction mixture is filtered
  4. customwhen the product crystallizes out
  5. filtrationThe product is filtered
  6. washwashed with methanol-ether mixture
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-38491a61eb7a48999c4aa4c65b76a891
Source dataset
uspto-grants-1986_04
Patent number
US04581458

Reaction notes

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