Tert-butyl 4-(methoxy(methyl)carbamoyl)-3-methylisothiazol-5-ylcarbamate → Tert-butyl 4-(4-chlorobenzoyl)-3-methylisothiazol-5-ylcarbamate

HRID 1772347Notes

Reaction equation

HRID 1772347 reaction equation
CON(C)[C:4]([C:6]1[C:7]([CH3:19])=[N:8][S:9][C:10]=1[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:5].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([Mg]Br)=[CH:24][CH:23]=1>C1COCC1>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:4]([C:6]2[C:7]([CH3:19])=[N:8][S:9][C:10]=2[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:5])=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 86706923Tert-butyl 4-(methoxy(methyl)carbamoyl)-3-methylisothiazol-5-ylcarbamateHCID 178478191HCID 178478191, compound

Product 1

HCID 67814309Tert-butyl 4-(4-chlorobenzoyl)-3-methylisothiazol-5-ylcarbamateYield 78.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-(methoxy(methyl)carbamoyl)-3-methylisothiazol-5-ylcarbamate (1.20 g, 3.98 mmol) in THF (30 mL) at −10° C. was added a solution of (4-chlorophenyl)magnesium bromide (1 M in diethylether) (11.95 mL, 11.95 mmol). After a period of 15 min, additional Grignard reagent was added (11.95 mL). After a period of 30 min, the reaction mixture was quenched with saturated ammonium chloride and EtOAc. The organic phase was separated, dried over Na2SO4, filtered and evaporated under reduced pressure. The resulting mixture was purified by flash chromatography (EtOAc/hexane 0:10 to 4:6) to give tert-butyl 4-(4-chlorobenzoyl)-3-methylisothiazol-5-ylcarbamate as an oil (1.1 g). LRMS (M+H)+: 353 m/z.

Workup

  1. waitAfter a period of 30 min
  2. customthe reaction mixture was quenched with saturated ammonium chloride and EtOAc
  3. customThe organic phase was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe resulting mixture was purified by flash chromatography (EtOAc/hexane 0:10 to 4:6)

Sources & evidence

ORD record
ord-f3aca48f26034a66abb6bb3fc03c5aae
Source dataset
uspto-grants-2016_02
Patent number
US09249161B2

Reaction notes

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