Water → HCID 19106477, compound

HRID 1197433Notes

Reaction equation

HRID 1197433 reaction equation
[CH3:1][CH:2]1[CH2:8][NH:7][CH2:6][C:5]2[CH:9]=[C:10]([S:12](=[O:15])(=[O:14])[NH2:13])[S:11][C:4]=2[S:3]1(=[O:17])=[O:16].[CH2:18](Br)[CH:19]([CH3:21])[CH3:20].C(N(CC)CC)C.O>CN(C)C=O>[CH3:1][CH:2]1[CH2:8][N:7]([CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:6][C:5]2[CH:9]=[C:10]([S:12](=[O:14])(=[O:15])[NH2:13])[S:11][C:4]=2[S:3]1(=[O:17])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 65551-Bromo-2-methylpropaneHCID 8471TriethylamineHCID 19106456HCID 19106456, compound

Product 1

HCID 19106477HCID 19106477, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2(R,S)-methyl-7-sulfamoyl-2,3,4,5-tetrahydrothieno[3,2-f]-1,4-thiazepin-1,1-dioxide (1.18 g, 4.0 mmol) in dry dimethylformamide (6 mL) containing isobutylbromide (1.3 mL, 12 mmol) and triethylamine (2.3 mL, 16 mmol) was warmed at 80° C. for 20 hours in a sealed tube. The reaction mixture was poured into water and the product extracted into ethyl acetate. This extract was dried (Na2SO4), filtered and evaporated. The residue was chromatographed on silica gel and eluted with a 0-1% methanol/chloroform gradient to give 900 mg (64%) of title compound which slowly crystallized. Recrystallization from methylene chloride/butyl chloride gave analytically pure material, mp 158°-159.5° C.

Workup

  1. extractionthe product extracted into ethyl acetate
  2. dry with materialThis extract was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was chromatographed on silica gel
  6. washeluted with a 0-1% methanol/chloroform gradient

Sources & evidence

ORD record
ord-4afffbc2284443c58bd625e856f3d46e
Source dataset
uspto-grants-1994_01
Patent number
US05276025

Reaction notes

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