Acetone → HCID 22736981, compound

HRID 51898Notes

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]COCC2)=[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.[CH3:30][C:31](C)=[O:32]>>[C:19]([NH:27][C:28]([NH:18][C:4]1[CH:5]=[C:6]([N:9]([CH3:17])[CH:10]2[CH2:11][CH2:16][O:32][CH2:31][CH2:30]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

Reactant 3

HCID 180Acetone

HCID 68284Benzoyl isothiocyanate

HCID 22736961HCID 22736961, compound

Product 1

HCID 22736981HCID 22736981, compoundYield 56%

Procedure

To a stirred solution of 0.330 g (1.4 mmol) 4-methoxy-N1-methyl-N1-(tetrahydro-pyran-4-ylmethyl)-benzene-1,3-diamine in 5 ml acetone was added dropwise 0.2 ml (1.50 mmol) benzoyl isothiocyanate and stirring continued for 16 hrs at room temperature. The mixture was then concentrated in vacuo and the residue subjected to column chromatography (1/1 hexane/ethyl acetate) to afford 0.31 g (56%) 1-benzoyl-3-{2-methoxy-5-[methyl-(tetrahydro-pyra n-4-yl)-amino]-phenyl}-thiourea as a yellow solid. ES-MS m/e (%): 422 (M+Na+, 13), 400 (M+H+, 100).

Workup

concentrationThe mixture was then concentrated in vacuo

Sources & evidence

ORD record: ord-3016e8fd107843b9b429362b01e49029
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713499B2

Reaction notes

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