Ethyl Acetate → 4-{3-[5-(5,6-Difluoro-1H-indol-2-yl)-2-methoxy-phenyl]-thioureido}-benzoic acid

HRID 25493

Reaction equation

HRID 25493 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][C:6]([C:12]1[CH:13]=[CH:14][C:15]([O:19][CH3:20])=[C:16]([NH2:18])[CH:17]=1)=[CH:5]2.[C:21]([C:24]1[CH:29]=[CH:28][C:27]([N:30]=[C:31]=[S:32])=[CH:26][CH:25]=1)([OH:23])=[O:22].C(OCC)(=O)C>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][C:6]([C:12]1[CH:13]=[CH:14][C:15]([O:19][CH3:20])=[C:16]([NH:18][C:31](=[S:32])[NH:30][C:27]3[CH:26]=[CH:25][C:24]([C:21]([OH:23])=[O:22])=[CH:29][CH:28]=3)[CH:17]=1)=[CH:5]2

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2429464-Isothiocyanatobenzoic acid2×HCID 99434395-(5,6-difluoro1H-indol-2-yl)-2-methoxy-phenylamine2×

Product 1

HCID 101150264-{3-[5-(5,6-Difluoro-1H-indol-2-yl)-2-methoxy-phenyl]-thioureido}-benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

The product from Example 3, 5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenylamine, (0.274 g, 1.0 mmol) was mixed with 4-carboxyphenyl isothiocyanate (0.183 g, 1.0 mmol) in tetrahydrofuran (10 mL) and was heated briefly to 50° C. and then allowed to stand overnight at room temperature. The tetrahydrofuran was boiled off on the rotary evaporator (no vacuum) to give a solid. Ethyl acetate (5 mL) was added, and the mixture was allowed to stand overnight at room temperature. The insoluble material was collected by filtration and was a mixture. All material from the reaction mixture was taken up in tetrahydrofuran/ethyl acetate and more 4-carboxyphenyl isothiocyanate (0.020 g, 0.11 mmol) was added and the solvent was boiled off on the rotary evaporator. Ethyl acetate was added to the solid and the mixture allowed to stand overnight at room temperature. The insoluble material was collected by filtration (0.191 g), mp 201-203° C.

Workup

  1. customThe tetrahydrofuran was boiled off on the rotary evaporator (no vacuum)
  2. customto give a solid
  3. waitto stand overnight at room temperature
  4. filtrationThe insoluble material was collected by filtration
  5. customthe solvent was boiled off on the rotary evaporator
  6. additionEthyl acetate was added to the solid
  7. waitto stand overnight at room temperature
  8. filtrationThe insoluble material was collected by filtration (0.191 g), mp 201-203° C.

Sources & evidence

ORD record
ord-0bb20bfbad2d47d092416d18cf09c6c3
Source dataset
uspto-grants-2005_02
Patent number
US06858739B2

Linked notes

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