4-Isothiocyanatobenzoic acid → 4-{3-[5-(1H-Indol-2-yl)-2-methoxy-phenyl]-thioureido}-benzoic acid

HRID 25518

Reaction equation

HRID 25518 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]([O:17][CH3:18])=[C:14]([NH2:16])[CH:15]=1.[C:19]([C:22]1[CH:27]=[CH:26][C:25]([N:28]=[C:29]=[S:30])=[CH:24][CH:23]=1)([OH:21])=[O:20]>O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]([O:17][CH3:18])=[C:14]([NH:16][C:29](=[S:30])[NH:28][C:25]2[CH:24]=[CH:23][C:22]([C:19]([OH:21])=[O:20])=[CH:27][CH:26]=2)[CH:15]=1

Participants

4

Reactant 2

HCID 2429464-Isothiocyanatobenzoic acidHCID 99002045-(1H-indol-2-yl)-2-methoxy-phenylamine2×

Product 1

HCID 101367294-{3-[5-(1H-Indol-2-yl)-2-methoxy-phenyl]-thioureido}-benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 1, Step B, 5-(1H-indol-2-yl)-2-methoxy-phenylamine (0.286 g, 1.0 mmol) was mixed with 4-carboxyphenyl isothiocyanate (0.185 g, 1.03 mmol) in tetrahydrofuran (40 mL). The solvent was boiled off on the rotary evaporator (no vacuum), and ethyl acetate was added to the residue and the insoluble material was collected by filtration. The collected solid was taken up in tetrahydrofuran, concentrated to dryness, and triturated again with ethyl acetate to give the product as a white solid (0.180 g), mp 201-203° C.

Workup

  1. customThe solvent was boiled off on the rotary evaporator (no vacuum), and ethyl acetate
  2. additionwas added to the residue
  3. filtrationthe insoluble material was collected by filtration
  4. concentrationconcentrated to dryness
  5. customtriturated again with ethyl acetate

Sources & evidence

ORD record
ord-59dd223e14d24fb2892d59c048dfbdde
Source dataset
uspto-grants-2005_02
Patent number
US06858739B2

Linked notes

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