2-Aminothiazole → 2H-(1)Benzothieno(2,3-e)-1,2-thiazine-3-carboxamide, 4-hydroxy-2-methyl-N-2-thiazolyl-, 1,1-dioxide

HRID 128254Notes

Reaction equation

HRID 128254 reaction equation
[OH:1][C:2]1[C:7]2[S:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[S:5](=[O:16])(=[O:15])[N:4]([CH3:17])[C:3]=1[C:18](OC)=[O:19].[S:22]1[CH:26]=[CH:25][N:24]=[C:23]1[NH2:27]>C1(C)C(C)=CC=CC=1>[OH:1][C:2]1[C:7]2[S:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[S:5](=[O:15])(=[O:16])[N:4]([CH3:17])[C:3]=1[C:18]([NH:27][C:23]1[S:22][CH:26]=[CH:25][N:24]=1)=[O:19]

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 547072593-carbomethoxy-4-hydroxy-2-methyl-2H-[1]benzothieno[2,3-e]-1,2-thiazine 1,1-dioxide

Product 1

HCID 546976412H-(1)Benzothieno(2,3-e)-1,2-thiazine-3-carboxamide, 4-hydroxy-2-methyl-N-2-thiazolyl-, 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

25.0 gm (0.0768 mol) of methyl 4-hydroxy-2-methyl-2H-[1]benzothieno-[2,3-e]-1,2-thiazine-3-carboxylate-1,1-dioxide and 10.0 gm (0.12 mol) of 2-thiazolamine were refluxed for 16 hours in 300 cc of anhydrous xylene in an atmosphere of nitrogen. The released methanol was removed by means of 4 A-molecular sieve filled in a Soxhlet apparatus. After cooling and standing for several hours, the reaction product was filtered off. After recrystallization from a mixture of dimethylformamide and 1,2-dichloroethane 19.9 gm (66% of theory) of light-yellow 4-hydroxy-2-methyl-N-(2-thiazolyl)-2H-[1]benzothieno[2,3-e]-1,2-thiazine-3-carboxamide-1,1-dioxide were obtained.

Workup

  1. customThe released methanol was removed by means of 4 A-molecular sieve
  2. additionfilled in a Soxhlet apparatus
  3. temperatureAfter cooling
  4. waitstanding for several hours
  5. filtrationthe reaction product was filtered off
  6. customAfter recrystallization
  7. additionfrom a mixture of dimethylformamide and 1,2-dichloroethane 19.9 gm (66% of theory) of light-yellow 4-hydroxy-2-methyl-N-(2-thiazolyl)-2H-[1]benzothieno[2,3-e]-1,2-thiazine-3-carboxamide-1,1-dioxide
  8. customwere obtained

Sources & evidence

ORD record
ord-ae0aa82799e64f5b98653853fbf4fb1a
Source dataset
uspto-grants-1981_03
Patent number
US04259336

Reaction notes

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