Ethyl isocyanate → 1-[4-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]-3-ethylurea, Hydrochloride

HRID 48251Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][CH:5]2[C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1.[CH2:21]([N:23]=[C:24]=[O:25])[CH3:22]>C1(C)C=CC=CC=1>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][CH:5]2[C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:24]([NH:23][CH2:21][CH3:22])=[O:25])=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

500 mg (1.63 mmol) of 4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylamine were introduced into 20 ml of toluene, and a solution of 284 mg (4.0 mmol) of ethyl isocyanate in a little toluene is added dropwise. After one hour at 80° C., a further 180 mg of ethyl isocyanate are added, and the mixture was stirred at 80° C. for one hour. For workup, the solvent was removed and the residue was triturated with H2O and ethyl acetate, filtered off with suction and dried, resulting in the title compound as a pale yellowish solid (m.p.: 218-220° C.). The ethylurea obtained in this way was converted into the corresponding hydrochloride in a manner known to the skilled worker.

Workup

customFor workup, the solvent was removed
customthe residue was triturated with H2O and ethyl acetate
filtrationfiltered off with suction
customdried

Sources & evidence

ORD record: ord-41ba9da4815a49be819dd54376093c4e
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06703405B2

Reaction notes

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