Dimethylformamide → HCID 15125473, compound

HRID 2106755Notes

Reaction equation

HRID 2106755 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][C:24]([CH3:27])=[N:25][N:26]=4)=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.Br[CH2:29][CH3:30].[OH-].[Na+].CN(C)C=O>O>[CH2:29]([N:26]1[N:25]=[C:24]([CH3:27])[S:23][C:22]1=[N:21][C:18]1[CH:19]=[CH:20][C:15]([N:12]2[CH2:11][CH2:10][N:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH2:14][CH2:13]2)=[CH:16][CH:17]=1)[CH3:30]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6332Ethyl BromideHCID 14798Sodium HydroxideHCID 15125471HCID 15125471, compound

Product 1

HCID 15125473HCID 15125473, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10.6 parts of N-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-5-methyl-1,3,4-thiadiazol-2-amine, 0.5 parts of bromoethane, 4 parts of sodium hydroxide pellets and 188 parts of N,N-dimethylformamide was stirred for 4 hours at 40°-50° C. After the addition of water, the crystallized product was filtered off and purified by column chromatography over silica gel using a mixture of trichloromethane, methanol, ethyl acetate and hexane (48:2:30:20 by volume) as eluent. The first 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 2.9 parts (25.3%) of N-(3-ethyl-5-methyl-1,3,4-thiadiazol-2(3H)-ylidene)-4-[4-(4-methoxyphenyl)-1-piperazinyl]benzenamine; mp. 175.4° C. (int. 14). 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 6.5 parts (56.7%) of N-ethyl-N-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-5-methyl-1,3,4-thiadiazol-2-amine; mp. 186.8° C. (int. 15).

Workup

  1. filtrationthe crystallized product was filtered off
  2. custompurified by column chromatography over silica gel using
  3. additiona mixture of trichloromethane, methanol, ethyl acetate and hexane (48:2:30:20 by volume) as eluent
  4. customThe first 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-3ac119e3b2f4453a8fcb80bd994c7db9
Source dataset
uspto-grants-1990_06
Patent number
US04931444

Reaction notes

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