N-methyl-N-(trimethylsilyl)trifluoroacetamide → N-(1,3-Dimorpholino-2-propyl)-1-methyl-4-imidazolesulfonamide

HRID 2253602Notes

Reaction equation

HRID 2253602 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH:8]([NH2:16])[CH2:9][N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH2:3][CH2:2]1.CN([Si](C)(C)C)C(=O)C(F)(F)F.[CH3:29][N:30]1[CH:34]=[C:33]([S:35](Cl)(=[O:37])=[O:36])[N:32]=[CH:31]1>ClCCl>[O:13]1[CH2:12][CH2:11][N:10]([CH2:9][CH:8]([NH:16][S:35]([C:33]2[N:32]=[CH:31][N:30]([CH3:29])[CH:34]=2)(=[O:37])=[O:36])[CH2:7][N:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 32510N-methyl-N-(trimethylsilyl)trifluoroacetamideHCID 27368871-methyl-1H-imidazole-4-sulfonyl chlorideHCID 123361941,3-Dimorpholino-2-propylamine

Product 1

HCID 9907561N-(1,3-Dimorpholino-2-propyl)-1-methyl-4-imidazolesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4 g (17.5 mmol) of 1,3-dimorpholino-2-propylamine and 3.5 g (17.5 mmol) of MSTFA [N-methyl-N-(trimethylsilyl)trifluoroacetamide] are combined under argon and stirred at room temperature for 17 hours. The clear solution is then concentrated in vacuo at 40° C./0.1 torr. A solution of 3.16 g (17.5 mmol) of 1-methyl-4-imidazolesulfonyl chloride in 20 ml of absolute dichloromethane is added at 20° C. with stirring to the oil obtained. After further stirring for 6 hours at 20° C., the solvent is distilled off in vacuo at 20° C./18 torr. The oil remaining crystallizes from isopropanol. After decolorization with active carbon, recrystallization from methanol/isopropanol gives the title compound of melting point 191°-192° C.

Workup

  1. concentrationThe clear solution is then concentrated in vacuo at 40° C./0.1 torr
  2. stirringwith stirring to the oil
  3. customobtained
  4. stirringAfter further stirring for 6 hours at 20° C.
  5. distillationthe solvent is distilled off in vacuo at 20° C./18 torr
  6. customThe oil remaining crystallizes from isopropanol
  7. customAfter decolorization with active carbon, recrystallization from methanol/isopropanol

Sources & evidence

ORD record
ord-eb919a6a4a8a4d69aba621c2f87120e0
Source dataset
uspto-grants-1993_08
Patent number
US05232922

Reaction notes

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