Hydrochloric Acid → 2-(4,7-Dimethoxy-5-acetylbenzofuran-6-yl)oxymethyl-4-isopropyl-6-methoxysaccharin

HRID 129058

Reaction equation

HRID 129058 reaction equation
Cl[CH2:2][N:3]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][C:9]([O:18][CH3:19])=[CH:10][C:11]=2[CH:15]([CH3:17])[CH3:16])[S:4]1(=[O:6])=[O:5].[CH3:20][O:21][C:22]1[C:27]2[CH:28]=[CH:29][O:30][C:26]=2[C:25]([O:31][CH3:32])=[C:24]([OH:33])[C:23]=1[C:34](=[O:36])[CH3:35].CN1NCCCCCCC(C2CCCCCCCCC=2)=N1.Cl>C(#N)C>[CH3:20][O:21][C:22]1[C:27]2[CH:28]=[CH:29][O:30][C:26]=2[C:25]([O:31][CH3:32])=[C:24]([O:33][CH2:2][N:3]2[C:13](=[O:14])[C:12]3[C:7](=[CH:8][C:9]([O:18][CH3:19])=[CH:10][C:11]=3[CH:15]([CH3:17])[CH3:16])[S:4]2(=[O:6])=[O:5])[C:23]=1[C:34](=[O:36])[CH3:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 68086Khellinone2×HCID 99951732-(Chloromethyl)-4-isopropyl-6-methoxybenzo[D]isothiazol-3(2H)-one 1,1-dioxide2×HCID 77320394Methyltriazabicyclodecene

Product 1

HCID 700458652-(4,7-Dimethoxy-5-acetylbenzofuran-6-yl)oxymethyl-4-isopropyl-6-methoxysaccharinYield 48.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Chloromethyl-4-isopropyl-6-methoxysaccharin (0.5 g) was added with stirring at room temperature to a solution of 4,7-dimethoxy-5-acetyl-6-hydroxybenzofuran (0.39 g) and methyltriazabicyclodecene (0.28 g) in acetonitrile (20 mL). The mixture was stirred overnight at room temperature. Since thin layer chromatography showed unreacted 4,7-dimethoxy-5-acetyl-6-hydroxybenzofuran, more 2-chloromethyl-4-isopropyl-6-methoxysaccharin and a drop of base were added, stirring was continued for a total of 24 hours, and the reaction mixture was poured into ice-water containing hydrochloric acid. The resulting golden solid was partially purified using dichloromethane as eluant The reaction was repeated with stirring overnight at 35°-40° C. instead of room temperature. The product and the partially purified product of the first reaction were combined and purified by column chromatography on silica gel affording 2-(4,7-dimethoxy-5-acetylbenzofuran-6-yl)oxymethyl-4-isopropyl-6-methoxysaccharin (0.4 g, 24% yield).

Workup

  1. additiona drop of base were added
  2. stirringstirring
  3. customwas continued for a total of 24 hours
  4. customThe resulting golden solid was partially purified
  5. stirringwith stirring overnight at 35°-40° C. instead of room temperature
  6. customThe product and the partially purified product of the first reaction
  7. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-409df9afce724b1ab441c2e40c7e0a2d
Source dataset
uspto-grants-1995_11
Patent number
US05466701

Linked notes

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