Benzoyl isothiocyanate → 1-Benzoyl-3-{2-methoxy-5-[methyl-(tetrahydro-pyran-4-ylmethyl)-amino]-phenyl}-thiourea

HRID 51890Notes

Reaction equation

HRID 51890 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH3:17])[CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:5][C:4]=1[NH2:18].[C:19]([N:27]=[C:28]=[S:29])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[C:19]([NH:27][C:28]([NH:18][C:4]1[CH:5]=[C:6]([N:9]([CH3:17])[CH2:10][CH:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])=[S:29])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 22736961HCID 22736961, compound

Product 1

HCID 227369731-Benzoyl-3-{2-methoxy-5-[methyl-(tetrahydro-pyran-4-ylmethyl)-amino]-phenyl}-thioureaYield 71.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 1.70 g (6.8 mmol) 4-methoxy-N1-methyl-N1-(tetrahydro-pyran-4-ylmethyl)-benzene-1,3-diamine in 30 ml acetone was added dropwise 1.0 ml (7.50 mmol) benzoyl isothiocyanate and stirring continued for 1 h at room temperature. The mixture was then concentrated in vacuo and the residue subjected to column chromatography (1/1 hexane/ethyl acetate) to afford 2.0 g (71%) 1-benzoyl-3-{2-methoxy-5-[methyl-(tetrahydro-pyran-4-ylmethyl)-amino]-phenyl}-thiourea as a yellow oil. ES-MS m/e (%): 436 (M+Na+, 13), 414 (M+H+, 100).

Workup

  1. concentrationThe mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-3fdd74b89777436aa73cbf69bd529932
Source dataset
uspto-grants-2004_03
Patent number
US06713499B2

Reaction notes

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