N-(4-bromo-3-methyl-5-isoxazolyl)-2-[N-methoxy(methylaminocarbonyl)]thiophene-3-sulfonamide → N-(4-bromo-3-methyl-5-isoxazolyl)-2-[(4-methylphenyl)acetyl]thiophene-3-sulfonamide

HRID 234473Notes

Reaction equation

HRID 234473 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][Mg]Cl)=[CH:4][CH:3]=1.[Br:11][C:12]1[C:13]([CH3:32])=[N:14][O:15][C:16]=1[NH:17][S:18]([C:21]1[CH:25]=[CH:24][S:23][C:22]=1[C:26](N(C)OC)=[O:27])(=[O:20])=[O:19]>C1COCC1>[Br:11][C:12]1[C:13]([CH3:32])=[N:14][O:15][C:16]=1[NH:17][S:18]([C:21]1[CH:25]=[CH:24][S:23][C:22]=1[C:26](=[O:27])[CH2:6][C:5]1[CH:9]=[CH:10][C:2]([CH3:1])=[CH:3][CH:4]=1)(=[O:19])=[O:20]

Participants

4

Reactant 2

HCID 10740291N-(4-bromo-3-methyl-5-isoxazolyl)-2-[N-methoxy(methylaminocarbonyl)]thiophene-3-sulfonamideHCID 178425359HCID 178425359, compound

Product 1

HCID 10695071N-(4-bromo-3-methyl-5-isoxazolyl)-2-[(4-methylphenyl)acetyl]thiophene-3-sulfonamideYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(4-bromo-3-methyl-5-isoxazolyl)-2-[(4-methylphenyl)acetyl]thiophene-3-sulfonamide was prepared in the same manner as described in Example 93B by reacting 4-methylbenzylmagnesium chloride with N-(4-bromo-3-methyl-5-isoxazolyl)-2-[N-methoxy(methylaminocarbonyl)]thiophene-3-sulfonamide in THF (see Example 93A) at -78° C. to room temperature, resulting in 78% yield. m.p. 146°-150° C.8

Workup

  1. customat -78° C. to room temperature
  2. customresulting in 78% yield

Sources & evidence

ORD record
ord-9274faed5ef343469f757eb4d66dcc4f
Source dataset
uspto-grants-1997_01
Patent number
US05594021

Reaction notes

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