O-Xylene → 4-Hydroxy-2-methyl-N-(2-pyridyl)-2H-[1]benzothieno[2,3-e]-1,2-thiazine-3-carboxamide-1,1-dioxide

HRID 1702623Notes

Reaction equation

HRID 1702623 reaction equation
[C:1]([C:5]1[N:6]([CH3:21])[S:7](=[O:20])(=[O:19])[C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[S:12][C:9]=2[C:10]=1[OH:11])(OC)=[O:2].[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1.C1(C)C(C)=CC=CC=1>CO>[OH:11][C:10]1[C:9]2[S:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:8]=2[S:7](=[O:19])(=[O:20])[N:6]([CH3:21])[C:5]=1[C:1]([NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)=[O:2]

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 104392-AminopyridineHCID 547072593-carbomethoxy-4-hydroxy-2-methyl-2H-[1]benzothieno[2,3-e]-1,2-thiazine 1,1-dioxide

Product 1

HCID 547072604-Hydroxy-2-methyl-N-(2-pyridyl)-2H-[1]benzothieno[2,3-e]-1,2-thiazine-3-carboxamide-1,1-dioxide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5 g. of 3-carbomethoxy-4-hydroxy-2-methyl-2H-[1]benzothieno[2,3-e]-1,2-thiazine 1,1-dioxide and 3 g. of 2-aminopyridine are treated with 150 ml. of a xylene isomer mixture and heated so that the resulting methanol distils off azeotropically. After 6 hours, the mixture is left to cool to room temperature. The cyrstals obtained are filtered off under suction and washed with a xylene mixture. After recrystallization from dimethylformamide and addition of methanol, there is obtained 4-hydroxy-2-methyl-N-(2-pyridyl)-2H-[1]benzothieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide in the form of yellow crystals of melting point 222°-224° C.

Workup

  1. customdistils off azeotropically
  2. waitthe mixture is left
  3. customThe cyrstals obtained
  4. filtrationare filtered off under suction
  5. washwashed with a xylene mixture
  6. customAfter recrystallization
  7. additionfrom dimethylformamide and addition of methanol

Sources & evidence

ORD record
ord-b27751292c2f41b59562839e868b0f30
Source dataset
uspto-grants-1982_09
Patent number
US04348519

Reaction notes

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