Water → 1-(3-methylphenyl)-3-[4-(1-oxo-2,3-dihydro-1H-isoindol-4-yl)phenyl]thiourea

HRID 1247462

Reaction equation

HRID 1247462 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH2:10][NH:11][C:12]3=[O:17])=[CH:4][CH:3]=1.[C:18]1([CH3:27])[CH:23]=[CH:22][CH:21]=[C:20]([N:24]=[C:25]=[S:26])[CH:19]=1.O>CN(C=O)C>[CH3:27][C:18]1[CH:19]=[C:20]([NH:24][C:25]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[CH:16]=[CH:15][CH:14]=[C:13]4[C:9]=3[CH2:10][NH:11][C:12]4=[O:17])=[CH:6][CH:7]=2)=[S:26])[CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 69304m-TolylisothiocyanateHCID 219075114-(4-Aminophenyl)isoindolin-1-one

Product 1

HCID 53298851-(3-methylphenyl)-3-[4-(1-oxo-2,3-dihydro-1H-isoindol-4-yl)phenyl]thioureaYield 43.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Example 1D (0.1 g, 0.44 mmol) in DMF (3 mL) was treated with m-tolylisothiocyanate (0.06 mL, 0.45 mmol), stirred at room temperature overnight, then cooled to 0° C., treated with water, and extracted twice with ethyl acetate. The combined extracts were washed with brine, dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel chromatography eluting with 3% methanol/dichloromethane to give 72 mg of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 2.30 (s, 3H); 4.53 (s, 2H); 6.96 (d, J=7.12 Hz, 1H); 7.23 (t, J=7.80 Hz, 1H); 7.29 (d, J=7.80 Hz, 2H); 7.57–7.69 (m, 7H); 8.68 (s, 1H); 9.84 (s, 1H); 9.88 (s, 1H); MS (ESI(−)) m/e 372 (M−H)−.

Workup

  1. temperaturecooled to 0° C.
  2. extractionextracted twice with ethyl acetate
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 3% methanol/dichloromethane

Sources & evidence

ORD record
ord-45b1eb922cfc46a0bad5a5bf646e7a74
Source dataset
uspto-grants-2006_10
Patent number
US07129260B2

Linked notes

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