Potassium Carbonate → N-[2-(4-methoxyphenyl)-1,3-dioxolan-2-ylmethyl]-N'-(2-methylpropyl)thiourea

HRID 484653

Reaction equation

HRID 484653 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([CH2:15][NH2:16])[O:14][CH2:13][CH2:12][O:11]2)=[CH:6][CH:5]=1.[N:17]([CH2:20][CH:21]([CH3:23])[CH3:22])=[C:18]=[S:19].C(=O)([O-])[O-].[K+].[K+]>CC(O)C>[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2([CH2:15][NH:16][C:18]([NH:17][CH2:20][CH:21]([CH3:23])[CH3:22])=[S:19])[O:11][CH2:12][CH2:13][O:14]2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68960Isobutyl isothiocyanateHCID 202717922-(4-Methoxyphenyl)-1,3-dioxolane-2-methanamine hydrochloride

Product 1

HCID 12833654N-[2-(4-methoxyphenyl)-1,3-dioxolan-2-ylmethyl]-N'-(2-methylpropyl)thioureaYield 89.65%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 22 parts of 2-(4-methoxyphenyl)-1,3-dioxolane-2-methanamine hydrochloride, 11.5 parts of 1-isothiocyanato-2-methylpropane, 20.7 parts of potassium carbonate and 200 parts of 2-propanol is stirred and refluxed for 3 hours. The reaction mixture is filtered while hot and the filtrate is evaporated. The solid residue is crystallized from a mixture of benzene and petroleumether. The product is filtered off and dried, yielding 26 parts (89.65%) of N-[2-(4-methoxyphenyl)-1,3-dioxolan-2-ylmethyl]-N'-(2-methylpropyl)thiourea; mp. 96° C.

Workup

  1. temperaturerefluxed for 3 hours
  2. filtrationThe reaction mixture is filtered while hot and the filtrate
  3. customis evaporated
  4. customThe solid residue is crystallized from a mixture of benzene and petroleumether
  5. filtrationThe product is filtered off
  6. customdried

Sources & evidence

ORD record
ord-82a1a1cef70c42ccbb4caa6c9fec2055
Source dataset
uspto-grants-1985_08
Patent number
US04533550

Linked notes

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