2-Amino-5-methylthiazole → HCID 54683005, compound

HRID 224603Notes

Reaction equation

HRID 224603 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10](=[O:12])(=[O:11])[N:9]([CH3:13])[C:8]([C:14]([O:16]C)=O)=[C:7]([OH:18])[C:6]=2[CH:19]=1.[NH2:20][C:21]1[S:22][C:23]([CH3:26])=[CH:24][N:25]=1>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10](=[O:11])(=[O:12])[N:9]([CH3:13])[C:8]([C:14]([NH:20][C:21]3[S:22][C:23]([CH3:26])=[CH:24][N:25]=3)=[O:16])=[C:7]([OH:18])[C:6]=2[CH:19]=1

Participants

4

Reactant 2

HCID 3517702-Amino-5-methylthiazoleHCID 54703139HCID 54703139, compound

Product 1

HCID 54683005HCID 54683005, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

5.0 gm (16.5 millimols) of methyl 6-chloro-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide and 2.1 gm (18.5 millimols) of 2-amino-5-methyl-thiazole were refluxed in 300 ml of anhydrous xylene for 24 hours in a Soxhlet-apparatus equipped with a 4-A-molecular sieve. After cooling, the crude product which had crystallized out was filtered off and recrystallized from dioxane. 4.9 gm (77% of theory) of 6-chloro-4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide were obtained.

Workup

  1. customequipped with a 4-A-molecular sieve
  2. temperatureAfter cooling
  3. customthe crude product which had crystallized out
  4. filtrationwas filtered off
  5. customrecrystallized from dioxane

Sources & evidence

ORD record
ord-98bd6dd378b24008b104a99a88bf6b80
Source dataset
uspto-grants-1980_11
Patent number
US04233299

Reaction notes

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