148550-96-3 → HCID 18963766, compound

HRID 2226876Notes

Reaction equation

HRID 2226876 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]2[S:7](=[O:17])[C:8]([C:14]([NH2:16])=[O:15])=[C:9](OC(C)C)[C:5]=2[CH:4]=1.C1(C2CCCCCCCCCC=2)CC[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][NH:22]N=1>NC1C=CC=CC=1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]2[S:7](=[O:17])[C:8]([C:14]([NH2:16])=[O:15])=[C:9]([NH:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:5]=2[CH:4]=1

Participants

5

Reactant 2

HCID 5481003148550-96-3HCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 18963766HCID 18963766, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 6115AnilineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-methoxy-(3-(1-methylethoxy))benzo[b]thiophene-2-carboxamide-1-oxide (250 mg, 0.89 mmol) and diazabicycloundecene (DBU) (664 μL, 4.4 mmol) in 5 mL of aniline is stirred at room temperature for 5 hours. The reaction mixture is diluted with ethyl acetate and washed with 1N HCl, saturated NaHCO3, and brine. The organic layer is dried over MgSO4, filtered, and concentrated in vacuo. Recrystallization from ethyl acetate:methanol gives 5-methoxy-3-(phenylamino)benzo[b]thiophene-2-carboxamide-1-oxide in 66% yield; mp=191°-192° C. dec.

Workup

  1. washwashed with 1N HCl, saturated NaHCO3, and brine
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-25e1dae287e440ad9ebcedad6b683225
Source dataset
uspto-grants-1994_09
Patent number
US05350748

Reaction notes

Loading…