Benzene → 3-[5-[1-(4-Chlorophenoxy)ethyl]-1,3,4-thiadiazol-2-yl]-1-methyl-1-(2,2-dimethoxyethyl)urea
Reaction equation
CC(C)[C:3](O)=[O:4].[CH3:7][NH:8][CH2:9][CH:10]=[O:11].[Cl:12][C:13]1[CH:29]=[CH:28][C:16]([O:17][CH:18]([C:20]2[S:24][C:23]([N:25]=[C:26]=[O:27])=[N:22][N:21]=2)[CH3:19])=[CH:15][CH:14]=1.[CH:30]1C=CC=CC=1>>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([O:17][CH:18]([C:20]2[S:24][C:23]([NH:25][C:26](=[O:27])[N:8]([CH3:7])[CH2:9][CH:10]([O:4][CH3:3])[O:11][CH3:30])=[N:22][N:21]=2)[CH3:19])=[CH:28][CH:29]=1Participants
Procedure
At ambient temperatures 3.9 grams (0.033 mole) of methylaminoacetaldehyde dimethylacetate was slowly added to a 30 ml. benzene solution containing 9.2 grams (0.033 mole) of the 5-[1-(4-chlorophenoxy)ethyl]-1,3,4-thiadiazol-2-yl isocyanate dimer (prepared above). The resulting solution was refluxed for 30 minutes to form a yellow solution and then cooled and topped with a roto-vac at 60 degrees centigrade to 12.4 grams of a viscous yellow oil which crystallized upon standing. The entire sample was recrystallized from a minimum amount of ethylacetate/hexane solution. The crystals were filtered off, and dried in a vacuum oven at 80 degrees centigrade to give 8.3 grams of fluffy white crystals of 3-[5-[1-(4-chlorophenoxy)ethyl-]-1,3,4-thiadiazol-2-yl]-1-methyl-1-1(2,2-dimethoxyethyl)urea. Melting point 116-118 degrees centigrade.
Workup
- temperatureThe resulting solution was refluxed for 30 minutes
- customto form a yellow solution
- temperaturecooled
- customcrystallized
- customThe entire sample was recrystallized from a minimum amount of ethylacetate/hexane solution
- filtrationThe crystals were filtered off
- customdried in a vacuum oven at 80 degrees centigrade
Sources & evidence
- ORD record
- ord-ed33bf100eb34cc08e30d86ba1e63a07
- Source dataset
- uspto-grants-1981_04
- Patent number
- US04264353
Reaction notes
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