Benzene → 3-[5-[1-(2,4-Dichlorophenoxy)ethyl]-1,3,4-thiadiazol-2-yl]-1-methyl-1-(2,2-dimethoxyethyl)urea

HRID 2287033Notes

Reaction equation

HRID 2287033 reaction equation
[CH3:1][O:2][CH:3]([O:7][CH3:8])[CH2:4][NH:5][CH3:6].C1C=CC=CC=1.[Cl:15][C:16]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:17]=1[O:18][CH:19]([C:21]1[S:25][C:24]([N:26]=[C:27]=[O:28])=[N:23][N:22]=1)[CH3:20]>CCCCCC.C(OCC)C>[Cl:15][C:16]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:17]=1[O:18][CH:19]([C:21]1[S:25][C:24]([NH:26][C:27](=[O:28])[N:5]([CH3:6])[CH2:4][CH:3]([O:7][CH3:8])[O:2][CH3:1])=[N:23][N:22]=1)[CH3:20]

Participants

5

Reactant 3

HCID 241BenzeneHCID 85032,2-DimethoxyethylmethylamineHCID 128800315-[1-(2,4-Dichlorophenoxy)ethyl]-1,3,4-thiadiazol-2-yl isocyanate

Product 1

HCID 128800323-[5-[1-(2,4-Dichlorophenoxy)ethyl]-1,3,4-thiadiazol-2-yl]-1-methyl-1-(2,2-dimethoxyethyl)ureaYield 81.7%

Reagents, catalysts & solvents 1

HCID 21584099Diethylether hexaneSolvent

Procedure

A 200 milliliter flask was charged with 2.1 grams (0.018 mole) of methylaminoacetaldehyde dimethylacetal, 50 milliliters of benzene and 5.8 grams (0.018 mole) of the 5-[1-(2,4-dichlorophenoxy)ethyl]-1,3,4-thiadiazol-2-yl isocyanate dimer (prepared above). The resulting slurry was refluxed for 15 minutes to form a yellow solution and cooled with formation of a few crystals. A minimum amount of hexane-diethylether was added, and crystallization occurred. The crystals were filtered off, and dried in a vacuum oven at 80°0 C. to give 6.4 grams of white crystals of 3-[5-[1-(2,4-dichlorophenoxy)-ethyl]-1,3,4-thiadiazol-2-yl]-1-methyl-1-(2,2-dimethoxyethyl)urea. (Melting point 125°-127° C.).

Workup

  1. temperatureThe resulting slurry was refluxed for 15 minutes
  2. customto form a yellow solution
  3. temperaturecooled with formation of a few crystals
  4. customcrystallization
  5. filtrationThe crystals were filtered off
  6. customdried in a vacuum oven at 80°0 C

Sources & evidence

ORD record
ord-d9663db54abc460781116b940447986e
Source dataset
uspto-grants-1981_05
Patent number
US04268675

Reaction notes

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