2,2-Dimethoxyethylmethylamine → N-(2,2-dimethoxyethyl)-N'-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-N-methylthiourea

HRID 648489Notes

Reaction equation

HRID 648489 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)=[C:2]=[S:3].[CH3:24][O:25][CH:26]([O:30][CH3:31])[CH2:27][NH:28][CH3:29]>ClCCl>[CH3:24][O:25][CH:26]([O:30][CH3:31])[CH2:27][N:28]([CH3:29])[C:2]([NH:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)=[S:3]

Participants

4

Reactant 2

HCID 85032,2-DimethoxyethylmethylamineHCID 155818991-(4-Isothiocyanatophenyl)-4-(4-methoxyphenyl)piperazine

Product 1

HCID 13732390N-(2,2-dimethoxyethyl)-N'-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-N-methylthioureaYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 15 parts of 1-(4-isothiocyanatophenyl)-4-(4-methoxyphenyl)piperazine, 6.5 parts of 2,2-dimethoxy-N-methylethanamine and 195 parts of dichloromethane was stirred for 1 hour at room temperature. The reaction mixture was evaporated and the residue was triturated in 4-methyl-2-pentanone. The product was filtered off and dried, yielding 19.4 parts (95%) of N-(2,2-dimethoxyethyl)-N'-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-N-methylthiourea; mp. 155.0° C. (40).

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was triturated in 4-methyl-2-pentanone
  3. filtrationThe product was filtered off
  4. customdried

Sources & evidence

ORD record
ord-236f003b40c0464fb486d8e013cc525f
Source dataset
uspto-grants-1988_04
Patent number
US04735942

Reaction notes

Loading…