Sodium hydride → HCID 23445570, compound

HRID 1166907Notes

Reaction equation

HRID 1166907 reaction equation
[Br:1][C:2]1[C:3]([CH3:8])=[N:4][O:5][C:6]=1[NH2:7].[H-].[Na+].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[CH2:16][C:17]1[S:21][C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[C:18]=1[S:26](Cl)(=[O:28])=[O:27]>C1COCC1>[Br:1][C:2]1[C:3]([CH3:8])=[N:4][O:5][C:6]=1[NH:7][S:26]([C:18]1[C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[S:21][C:17]=1[CH2:16][C:15]1[CH:30]=[CH:31][C:32]([O:33][CH3:34])=[C:13]([O:12][CH3:11])[CH:14]=1)(=[O:27])=[O:28]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 104875194-Bromo-3-methylisoxazol-5-amineHCID 22998461HCID 22998461, compound

Product 1

HCID 23445570HCID 23445570, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(4-bromo-3-methyl-5-isoxazolyl)-2-(3,4-dimethoxy-benzyl)-benzo[b]thiophene-3-sulfonamide was prepared in the same manner as described in Example 41. Reaction of 4-bromo-3-methyl-5-aminoisoxazole (1.0 mmoles, 0.18 g), NaH (2.5 mmoles, 60 mg), and 2-(3,4-dimethoxybenzyl)benzo[b]thiophene-3-sulfonylchloride (1.2 mmoles, 0.44 g) in THF (6 ml), after recrystallization from chloroform and hexanes, yielded 0.42 g (80%) of a brown solid, m.p. 151-153° C.

Workup

  1. customafter recrystallization from chloroform and hexanes

Sources & evidence

ORD record
ord-cf75105bf4884f859dcbc13ec74a5202
Source dataset
uspto-grants-2003_09
Patent number
US06613804B2

Reaction notes

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