2-Chloroacetophenone → N-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-4-phenyl-2-thiazolamine

HRID 2106747Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH2:24])=[S:23])=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.Cl[CH2:26][C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=O.C([O-])(=O)C.[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22]4[S:23][CH:26]=[C:27]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[N:24]=4)=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5 parts of N-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]thiourea, 3 parts of 2-chloro-1-phenylethanone, 1.7 parts of sodium acetate and 100 parts of acetic acid was stirred for 4 hours at 80° C. After cooling, the reaction mixture was evaporated and the residue was stirred in 130 parts of dichloromethane. The whole was neutralised with a sodium hydrogen carbonate solution. The precipitated product was filtered off, washed with water and dichloromethane and crystallized from 1,4-dioxane. The product was filtered off and dried, yielding 4.5 parts (69.6%) of N-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-4-phenyl-2-thiazolamine; mp. 269.7° C. (int. 2).

Workup

temperatureAfter cooling
customthe reaction mixture was evaporated
stirringthe residue was stirred in 130 parts of dichloromethane
filtrationThe precipitated product was filtered off
washwashed with water and dichloromethane
customcrystallized from 1,4-dioxane
filtrationThe product was filtered off
customdried

Sources & evidence

ORD record: ord-c6a228a124e34143a15f46e28a121744
Source dataset: uspto-grants-1990_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04931444

Reaction notes

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