Dimethylformamide → HCID 70373800, compound

HRID 2106750Notes

Reaction equation

HRID 2106750 reaction equation
[CH3:1][O:2][CH:3]1[S:7][C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][N:18]([C:21]4[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=4)[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=[N:5][CH2:4]1.Br[CH2:30][CH3:31].[OH-].[Na+].CN(C)C=O>O>[OH2:2].[CH2:30]([N:8]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:16][CH2:17][N:18]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[CH2:19][CH2:20]2)=[CH:11][CH:10]=1)[C:6]1[S:7][CH:3]([O:2][CH3:1])[CH2:4][N:5]=1)[CH3:31].[CH2:30]([N:8]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:16][CH2:17][N:18]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[CH2:19][CH2:20]2)=[CH:11][CH:10]=1)[C:6]1[S:7][CH:3]([O:2][CH3:1])[CH2:4][N:5]=1)[CH3:31]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6332Ethyl BromideHCID 14798Sodium HydroxideHCID 15125465HCID 15125465, compound

Product 1

HCID 70373800HCID 70373800, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 15 parts of 4,5-dihydro-5-methoxy-N-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-2-thiazolamine, 5.8 parts of bromoethane, 3 parts of sodium hydroxide pellets and 207 parts of N,N-dimethylformamide was stirred for 16 hours at room temperature. The reaction mixture was diluted with water. The precipitated product was filtered off and purified by column chromatography over silica gel using a mixture of trichloromethane, ethyl acetate, hexane and methanol (49::30:20:1 by volume) as eluent. The second fraction was collected and the eluent was evaporated. The residue was crystallized from 4-methyl-2-pentanone. The product was filtered off and dried, yielding 7.3 parts (44.4%) of N-ethyl-4,5-dihydro-5-methoxy-N-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-2-thiazolamine hemihydrate; mp. 131.5° C. (int. 6).

Workup

  1. filtrationThe precipitated product was filtered off
  2. custompurified by column chromatography over silica gel using
  3. additiona mixture of trichloromethane, ethyl acetate, hexane and methanol (49::30:20:1 by volume) as eluent
  4. customThe second fraction was collected
  5. customthe eluent was evaporated
  6. customThe residue was crystallized from 4-methyl-2-pentanone
  7. filtrationThe product was filtered off
  8. customdried

Sources & evidence

ORD record
ord-1057638850474169ade3d66b3430dcff
Source dataset
uspto-grants-1990_06
Patent number
US04931444

Reaction notes

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