Dimethylformamide dimethyl acetal → HCID 70392841, compound

HRID 1383005Notes

Reaction equation

HRID 1383005 reaction equation
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[OH:9][CH2:10][C:11]1[N:16]=[CH:15][C:14]2[CH:17]=[C:18]([S:20](=[O:23])(=[O:22])[NH2:21])[O:19][C:13]=2[CH:12]=1>C(#N)C.C(Cl)(Cl)Cl>[CH3:6][N:4]([CH3:5])[CH:3]=[N:21][S:20]([C:18]1[O:19][C:13]2[CH:12]=[C:11]([CH2:10][OH:9])[N:16]=[CH:15][C:14]=2[CH:17]=1)(=[O:22])=[O:23]

Participants

5

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 14372115HCID 14372115, compound

Product 1

HCID 70392841HCID 70392841, compoundYield 48.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

N,N-Dimethylformamide dimethyl acetal (1.0 ml, 0.007 mole) was added dropwise (10 minutes) to a suspension of 6-hydroxymethyl-2-sulfamoylfuro[3,2-c]pyridine (1.33 g, 0.005% mole) in acetonitrile (25 ml). The mixture was stirred at room temperature under N2 for 40 hours. The reaction mixture was diluted with CHCl3 and washed with water. The organic phase was separated, dried (Na2SO4) and filtered through charcoal. The filtrate was concentrated to dryness and the residue recrystallized from ethyl acetate to give the product as a yellow solid 0.8 g (48% yield). Recrystallization from methanol/ethyl acetate gave an analytical sample, mp: 161°-163° C.

Workup

  1. washwashed with water
  2. customThe organic phase was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered through charcoal
  5. concentrationThe filtrate was concentrated to dryness
  6. customthe residue recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e95aaecf74a449029c82d4f3d2b24dd0
Source dataset
uspto-grants-1989_02
Patent number
US04808595

Reaction notes

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