Phenylacetyl chloride → HCID 86611255, compound

HRID 908320Notes

Reaction equation

HRID 908320 reaction equation
[CH3:1][O:2][C:3]1C=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1.C1(CC([N:29]=[C:30]=[S:31])=O)C=CC=CC=1.[C:32]1([CH2:38][C:39](Cl)=[O:40])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[N:42]([K])=C=S>CC#N.CO>[CH3:1][O:2][C:3]1[CH:6]=[CH:7][C:8]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:30]([NH:29][C:39](=[O:40])[CH2:38][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[S:31])=[CH:15][CH:14]=2)=[C:9]2[C:4]=1[CH:5]=[N:42][CH:11]=[CH:10]2

Participants

7

Reactant 4

HCID 7679Phenylacetyl chlorideHCID 12454157Phenylacetyl isothiocyanateHCID 67386888HCID 67386888, compoundHCID 178528018HCID 178528018, compound

Product 1

HCID 86611255HCID 86611255, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 4-(5-methoxynaphthalen-1-yl)benzenamine (140 mg, 0.56 mmol) and 2-phenylethanoyl isothiocyanate (320 mg, 1.98 mmol), prepared by condensing 2-phenylacetyl chloride and isothiocyanatopotassium in MeCN at 80° C., in MeOH (5 mL) was stirred at room temperature overnight. The reaction mixture quenched with NaHCO3 (aq. 10 mL) and extracted with dichloromethane 3×5 mL. The combined organic phase was dried over Na2SO4, and concentrated, and purified on silica with 3% MeOH in dichloromethane to afford 1-(4-(8-methoxyisoquinolin-5-yl)phenyl)-3-(2-phenylacetyl)thiourea as a yellow solid (25 mg, 11%). MS (ESI pos. ion) m/z: 428 (M+H). 1 (a) Hendrickson, J. B.; Radriguez, C. J. Org. Chem. 1983, 48, 3344-3346. (b) S-Y Sit, et al. Bioorg. Med. Chem., 2004, 12, 715-736.

Workup

  1. customThe reaction mixture quenched with NaHCO3 (aq. 10 mL)
  2. extractionextracted with dichloromethane 3×5 mL
  3. dry with materialThe combined organic phase was dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified on silica with 3% MeOH in dichloromethane

Sources & evidence

ORD record
ord-b6c91bc4c56a4a07aaf26ce5f8f57116
Source dataset
uspto-grants-2011_09
Patent number
US08017601B2

Reaction notes

Loading…