Tert-butyl 4-(4-chlorobenzoyl)-3-methylisothiazol-5-ylcarbamate → (5-Amino-3-methylisothiazol-4-yl)(4-chlorophenyl)methanone

HRID 1772348Notes

Reaction equation

HRID 1772348 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([C:8]2[C:9]([CH3:21])=[N:10][S:11][C:12]=2[NH:13]C(=O)OC(C)(C)C)=[O:7])=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O>[NH2:13][C:12]1[S:11][N:10]=[C:9]([CH3:21])[C:8]=1[C:6]([C:5]1[CH:22]=[CH:23][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:7]

Participants

3

Reactant 1

HCID 67814309Tert-butyl 4-(4-chlorobenzoyl)-3-methylisothiazol-5-ylcarbamate

Product 1

HCID 67814140(5-Amino-3-methylisothiazol-4-yl)(4-chlorophenyl)methanoneYield 74.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To tert-butyl 4-(4-chlorobenzoyl)-3-methylisothiazol-5-ylcarbamate (2.80 g, 7.94 mmol) was added an excess of TFA (20 mL). After a period of 15 min at reflux, the reaction mixture was evaporated under reduced pressure to give (5-amino-3-methylisothiazol-4-yl)(4-chlorophenyl)methanone as a white solid (1.50 g).

Workup

  1. temperatureAfter a period of 15 min at reflux
  2. customthe reaction mixture was evaporated under reduced pressure

Sources & evidence

ORD record
ord-17cae3036e9141de9da3f527d97d94ad
Source dataset
uspto-grants-2016_02
Patent number
US09249161B2

Reaction notes

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