Water → HCID 89704920, compound

HRID 929017Notes

Reaction equation

HRID 929017 reaction equation
[NH2:1][C:2]1[C:11]([S:12]CC2C=CC(OC)=CC=2)=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])[C:3]=1[F:30].C([C:33]1[C:39](=O)[C:38](Cl)=[C:37]([Cl:42])[C:35](=O)[C:34]=1C#N)#N.[OH2:45]>C(Cl)Cl>[S:12]([C:11]1[C:2]([NH2:1])=[C:3]([F:30])[C:4]([NH:22][C:35]2[CH:34]=[CH:33][CH:39]=[CH:38][C:37]=2[Cl:42])=[C:5]([CH:10]=1)[C:6]([O:8][CH3:9])=[O:45])[S:12][C:11]1[C:2]([NH2:1])=[C:3]([F:30])[C:4]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])=[C:5]([CH:10]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 89705068HCID 89705068, compound

Product 1

HCID 89704920HCID 89704920, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-amino-5-(4-methoxybenzylthio)-3-fluoro-2-((2-chlorophenyl)amino)benzoate (19.93 g, 44.6 mmol) in CH2Cl2 (180 mL) was added DDQ (11.25 g, 53.73 mmol) followed by water (20 mL). After stirring at ambient temperature for 10 h, the reaction was quenched by saturated sodium bicarbonate (aq., 100 mL). The aqueous layer was extracted by CH2Cl2 (100 mL×3). The combined organic phase was washed with water (100 mL) and brine (100 mL) sequentially, dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 5:1, v/v) to give the desired product (pale yellow solid, 9.39 g, 32.3% yield). 1H NMR (400 MHz, CDCl3): δ 9.33 (s, 2H), 7.46 (s, 2H), 7.40 (m, 2H), 7.15 (m, 2H), 6.92 (m, 2H), 6.76 (m, 2H), 4.86 (br, 4H), 3.80 (s, 6H).

Workup

  1. customthe reaction was quenched by saturated sodium bicarbonate (aq., 100 mL)
  2. extractionThe aqueous layer was extracted by CH2Cl2 (100 mL×3)
  3. washThe combined organic phase was washed with water (100 mL) and brine (100 mL) sequentially
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 5:1

Sources & evidence

ORD record
ord-cec65d41ce754174b4bab38c83b7c1d8
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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