p-Toluenesulfonic acid → HCID 9887694, compound

HRID 428009Notes

Reaction equation

HRID 428009 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13](=[O:20])[C:14]3[S:19][CH:18]=[CH:17][C:15]=3[N:16]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([NH:16][C:15]2[CH:17]=[CH:18][S:19][C:14]=2[C:13]([NH:29][C:26]2[CH:27]=[CH:28][C:23]([O:22][CH3:21])=[CH:24][CH:25]=2)=[O:20])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7732P-AnisidineHCID 10684544HCID 10684544, compound

Product 1

HCID 9887694HCID 9887694, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-[4-(tert-butyl)phenyl]-4-oxo-4H-thieno[3,2-d][1.3]oxazine (60 mg, 0.21 mmol) and p-anisidine (26 mg, 0.21 mmol) in toluene (1 mL) was treated with p-toluenesulfonic acid (4 mg) and the resulting mixture heated at relux for 30 h. The mixture was concentrated in vacuo and the residue was purified by flash chromatography (silica gel, hexanes/ethyl acetate) to yield 35 mg (41%) of the title compound.

Workup

  1. temperaturethe resulting mixture heated at relux for 30 h
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was purified by flash chromatography (silica gel, hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-fe8de2f922644275b3385762ea528aff
Source dataset
uspto-grants-2001_11
Patent number
US06313151B1

Reaction notes

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