Benzoyl isothiocyanate → HCID 59603075, compound

HRID 2068706Notes

Reaction equation

HRID 2068706 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH3:17])=[CH:11][C:12]([Br:16])=[C:13]([NH2:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]([N:26]=[C:27]=[S:28])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(C)=O>[C:18]([NH:26][C:27]([NH:15][C:13]1[CH:14]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:10]([CH3:17])=[CH:11][C:12]=1[Br:16])=[S:28])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 70180235-(benzyloxy)-2-bromo-4-methylaniline

Product 1

HCID 59603075HCID 59603075, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 5-benzyloxy-2-bromo-4-methyl-phenylamine (0.50 g, 1.71 mmol) in acetone (20 mL) was added benzoylisothiocyanate (0.28 mL, 2.08 mmol) dropwise at room temperature. The resulting reaction mixture was stirred for 30 min. at the same temperature. After completion of reaction (TLC monitoring), acetone was distilled off, the solid residue was stirred in hexane for 5-10 min and then filtered to obtain the desired product as white solid (0.70 g, 88%). 1H NMR (400 MHz, DMSO-d6): δ 2.20 (s, 3H), 5.10 (s, 2H), 7.33 (m, 1H), 7.40 (t, J=7.20 Hz, 2H), 7.48 (d, J=7.60 Hz, 2H), 7.55 (m, 3H), 7.67 (m, 1H), 7.73 (s, 1H), 8.0 (d, J=7.20 Hz, 2H), 11.81 (br s, 1H) and 12.59 (br s, 1H).

Workup

  1. customThe resulting reaction mixture
  2. distillationwas distilled off
  3. stirringthe solid residue was stirred in hexane for 5-10 min
  4. filtrationfiltered

Sources & evidence

ORD record
ord-f927e7034b9e4aaca502d349e1e301d1
Source dataset
uspto-grants-2012_10
Patent number
US08299065B2

Reaction notes

Loading…