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

HRID 2106748Notes

Reaction equation

HRID 2106748 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]4[S:23][CH:24]=[C:25]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[N:26]=4)=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.Br[CH2:34][CH3:35].[OH-].[Na+].CN(C)C=O>O>[CH2:34]([N:21]([C:18]1[CH:17]=[CH:16][C:15]([N:12]2[CH2:11][CH2:10][N:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[CH2:14][CH2:13]2)=[CH:20][CH:19]=1)[C:22]1[S:23][CH:24]=[C:25]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:26]=1)[CH3:35]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6332Ethyl Bromide2×HCID 14798Sodium Hydroxide2×HCID 15125462N-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-4-phenyl-2-thiazolamine

Product 1

HCID 15125463N-ethyl-N-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-4-phenyl-2-thiazolamineYield 81.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.6 parts of N-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-4-phenyl-2-thiazolamine, 2 parts of bromoethane, 1 part of sodium hydroxide and 94 parts of N,N-dimethylformamide was stirred for 16 hours at room temperature. Another portion of 2 parts of bromoethane and 1 part of sodium hydroxide was added and stirring was continued for 4 hours at 50° C. The reaction mixture was diluted with water. The precipitated product was filtered off and purified by column chromatography over silica gel using trichloromethane as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 4-methyl-2-pentanone. The product was filtered off and dried, yielding 4.0 parts (81.7%) of N-ethyl-N-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-4-phenyl-2-thiazolamine; mp. 223.6° C. (int. 3).

Workup

  1. stirringstirring
  2. waitwas continued for 4 hours at 50° C
  3. filtrationThe precipitated product was filtered off
  4. custompurified by column chromatography over silica gel
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated
  7. customThe residue was crystallized from 4-methyl-2-pentanone
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-111b4fac7d714f04a8a52f2ebfdcf6e4
Source dataset
uspto-grants-1990_06
Patent number
US04931444

Reaction notes

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