Ammonium Chloride → HCID 22313976, compound

HRID 270462Notes

Reaction equation

HRID 270462 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][C:15]([O:17][CH2:18][C:19](N(OC)C)=[O:20])=[CH:16][C:11]=3[S:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:25][Mg]Br.[NH4+].[Cl-]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][C:15]([O:17][CH2:18][C:19](=[O:20])[CH3:25])=[CH:16][C:11]=3[S:10][N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 22313917HCID 22313917, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 22313976HCID 22313976, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 208 mg (0.51 mmol) 2-[3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yloxy]-N-methoxy-N-methyl-acetamide in 8 ml THF were added 0.51 ml 3M (1.53 mmol, 3 eq) methylmagnesiumbromide in THF at −75° C. The solution was slowly warmed to RT over night, a saturated aqueous solution of NH4Cl was added and the mixture stirred for 30 min. The phases were separated and the inorganic phase was extracted with EtOAc. The combined organic phases were dried over Na2SO4 and evaporated. Column chromatography on silica gel with EtOAc:hexane 1:4 yielded 109 mg (53%) 1-[3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yloxy]-propan-2-one as white solid, MS: 361 (M, 1Br).

Workup

  1. customThe phases were separated
  2. extractionthe inorganic phase was extracted with EtOAc
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-99c311875f184827a4f2d35a64470a06
Source dataset
uspto-grants-2008_11
Patent number
US07449483B2

Reaction notes

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