Water → HCID 67040855, compound

HRID 605248Notes

Reaction equation

HRID 605248 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:19])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N:16]([CH3:18])[CH3:17])[CH:11]=2)=[CH:4][C:3]=1[N+:20]([O-:22])=[O:21].C([O-])([O-])=O.[K+].[K+].[NH2:29][C:30]1[CH:35]=[CH:34][C:33]([SH:36])=[CH:32][CH:31]=1.O>CN(C=O)C>[NH2:29][C:30]1[CH:35]=[CH:34][C:33]([S:36][C:2]2[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:19])[C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([N:16]([CH3:18])[CH3:17])[CH:11]=3)=[CH:4][C:3]=2[N+:20]([O-:22])=[O:21])=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 145104-AminothiophenolHCID 24099019HCID 24099019, compound

Product 1

HCID 67040855HCID 67040855, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of Example 239b (5.0 g, 15.6 mmol) in DMF (50 mL) was added K2CO3 (4.3 g, 17.0 mmol) and 4-aminothiophenol (1.9 g, 8.5 mmol). The mixture was heated at 65° C. for 16 h. The reaction was cooled and poured into water. The aqueous phase was extracted with ethyl acetate (2×). The combined organic phases were washed with water, brine, and dried over sodium sulfate, filtered and concentrated under vacuum giving the title compound. The residue was purified by silica gel chromatography eluting with hexanes/ethyl acetate/methanol (50:40:10) to give the desired product (3.4 g, 53%).

Workup

  1. temperatureThe reaction was cooled
  2. extractionThe aqueous phase was extracted with ethyl acetate (2×)
  3. washThe combined organic phases were washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5c108b7aac064bcdac1084be808bfd6b
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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