2-Aminothiazole → HCID 20492766, compound

HRID 434496Notes

Reaction equation

HRID 434496 reaction equation
C(O[C:4]([CH:6]1[C:11](=[O:12])[N:10]([CH3:13])[C:9]2[CH:14]=[CH:15][CH:16]=[CH:17][C:8]=2[S:7]1)=[O:5])C.[NH2:18][C:19]1[S:20][CH:21]=[CH:22][N:23]=1>C1(C)C(C)=CC=CC=1>[CH3:13][N:10]1[C:9]2[CH:14]=[CH:15][CH:16]=[CH:17][C:8]=2[S:7][CH:6]([C:4](=[O:5])[NH:18][C:19]2[S:20][CH:21]=[CH:22][N:23]=2)[C:11]1=[O:12]

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 20492733HCID 20492733, compound

Product 1

HCID 20492766HCID 20492766, compoundYield 15.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 2-ethoxycarbonyl-4-methyl-2H-1,4-benzothiazin-3(4H)one (6.22 g), 2-aminothiazole (7.43 g), and xylene (31 ml) was refluxed for 6 hours. After being cooled, the mixture was washed with 10% hydrochloric acid, water, dried over magnesium sulfate, and evaporated under reduced pressure. The residue was crystallized from diethyl ether and collected by filtration. The crude crystals were purified by recrystallization from acetonitrile to yield 1.17 g of 4-methyl-2-(2-thiazolylcarbamoyl)-2H-1,4-benzothiazin-3(4H)one.

Workup

  1. temperaturewas refluxed for 6 hours
  2. temperatureAfter being cooled
  3. washthe mixture was washed with 10% hydrochloric acid, water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was crystallized from diethyl ether
  7. filtrationcollected by filtration
  8. customThe crude crystals were purified by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-33f68ccf467843a7bcc665c917e755c7
Source dataset
uspto-grants-1983_08
Patent number
US04397849

Reaction notes

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