Water → HCID 67040679, compound

HRID 605244Notes

Reaction equation

HRID 605244 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19].[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([SH:28])=[CH:24][CH:23]=1.O>CN(C=O)C>[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([S:28][C:2]2[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:17])[C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[CH:4][C:3]=2[N+:18]([O-:20])=[O:19])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 145104-AminothiophenolHCID 871352HCID 871352, compound

Product 1

HCID 67040679HCID 67040679, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of Example 238b (2.5 g, 8.5 mmol) in DMF (50 mL) was added CsCO3 (5.5 g, 17.0 mmol), and 4-aminothiophenol (1.0 g, 8.5 mmol). The mixture was heated at 80° 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 (60:30:10) to give the desired product (1.5 g, 46%).

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-f65d7a8d091f41b78d43e894d3042908
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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