Benzoyl isothiocyanate → N-(2-methoxy-5-morpholinophenylcarbamothioyl)benzamide

HRID 2220831Notes

Reaction equation

HRID 2220831 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:5][C:4]=1[NH2:15].[C:16]([N:24]=[C:25]=[S:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC(C)=O>[C:16]([NH:24][C:25]([NH:15][C:4]1[CH:5]=[C:6]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])=[S:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 113677782-Methoxy-5-morpholinoaniline

Product 1

HCID 22015734N-(2-methoxy-5-morpholinophenylcarbamothioyl)benzamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 2-methoxy-5-morpholin-4-yl-phenylamine (4.6 g, 22 mmol) in acetone (140 ml) is added a solution of benzoyl isothiocyanate (3.4 ml, 25 mmol) in acetone (80 ml) and the reaction mixture is stirred for further 30 min at ambient temperature. After removal of the volatile components in vacuo, the product is isolated by flash chromatography (silica, eluent ethyl acetate/n-hexane 1:4, then 1:2) as a yellow solid (8.0 g, 97%). MS: m/e=272 (M+).

Workup

  1. customAfter removal of the volatile components in vacuo
  2. customthe product is isolated by flash chromatography (silica, eluent ethyl acetate/n-hexane 1:4

Sources & evidence

ORD record
ord-8fd21ce0cc1d46a898e0816216907cab
Source dataset
uspto-grants-2008_05
Patent number
US07368446B2

Reaction notes

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