Dimethylamine → HCID 22406968, compound

HRID 440328Notes

Reaction equation

HRID 440328 reaction equation
[CH3:1][NH:2][CH3:3].[O:4]([CH:12]([C:17]1[S:18][C:19]([S:22]([NH2:25])(=[O:24])=[O:23])=[CH:20][N:21]=1)[CH2:13][CH2:14][CH2:15]I)[Si](C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:4][CH:12]([C:17]1[S:18][C:19]([S:22]([NH2:25])(=[O:24])=[O:23])=[CH:20][N:21]=1)[CH2:13][CH2:14][CH2:15][N:2]([CH3:3])[CH3:1]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 2724141Tetrabutylammonium FluorideHCID 54469457HCID 54469457, compound

Product 1

HCID 22406968HCID 22406968, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dimethylamine was bubbled through a solution of 2-(1-t-butyldimethylsiloxy-4-iodobutyl)-5-thiazole sulfonamide (0.78 mmol, 0.37 g ) in THF (8 mL) at 0° C. After 30 minutes the solvent was removed and the residue taken up in THF and TBAF (1.17 mmol) added. The reaction was stirred at rt for 2 hours. The reaction was concentrated and the residue subjected to flash chromatography (5% MeOH/NH3 /CHCl3) to afford 0.16 g (72%) of 2-(1-hydroxy-4-(N,N-dimethylamino)butyl)-5-thiazole sulfonamide.

Workup

  1. customAfter 30 minutes the solvent was removed
  2. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-6f2ab48d0e7442b9a5a8bc05e5cd506c
Source dataset
uspto-grants-1996_05
Patent number
US05519040

Reaction notes

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