Isopropyl iodide → HCID 70199106, compound

HRID 342450Notes

Reaction equation

HRID 342450 reaction equation
[NH2:1][C:2]1[C:7]2[O:8][C:9]([CH3:15])=[C:10]([C:11]([OH:14])([CH3:13])[CH3:12])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[N+:16]([C:19]1[CH:29]=[CH:28][CH:27]=[C:21]2[C:22]([O:24][C:25](=[O:26])[C:20]=12)=[O:23])([O-:18])=[O:17].C(=O)([O-])[O-].[K+].[K+].[CH:36](I)([CH3:38])[CH3:37]>CN(C)C=O>[OH:14][C:11]([C:10]1[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([NH:1][C:25](=[O:26])[C:20]3[C:21]([C:22]([O:24][CH:36]([CH3:38])[CH3:37])=[O:23])=[CH:27][CH:28]=[CH:29][C:19]=3[N+:16]([O-:18])=[O:17])[C:7]=2[O:8][C:9]=1[CH3:15])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 216313-Nitrophthalic anhydrideHCID 70200213HCID 70200213, compound

Product 1

HCID 70199106HCID 70199106, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-amino-3-(1-hydroxy-l-methylethyl)-2-methylbenzo[b]furan (150 mg), 3-nitrophthalic anhydride (205 mg) and potassium carbonate (202 mg) in N,N-dimethylformamide (2 ml) was stirred at ambient temperature for 2 hours. Then, isopropyl iodide (280 mg) was added to the mixture and the mixture was stirred for 3 hours. The mixture was partitioned between ethyl acetate and brine. The organic layer was separated, dried over sodium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel and the obtained oil was crystallized from a mixture of 2-propanol and water to give 3-(1-hydroxy-1-methylethyl)-7-(6-isopropoxycarbonyl-2-nitrobenzoylamino)-2-methylbenzo[b]furan (136 mg).

Workup

  1. stirringthe mixture was stirred for 3 hours
  2. customThe mixture was partitioned between ethyl acetate and brine
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel
  7. customthe obtained oil was crystallized from a mixture of 2-propanol and water

Sources & evidence

ORD record
ord-ed249e175ffc45258f13bff5b820990c
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

Loading…