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

HRID 224524Notes

Reaction equation

HRID 224524 reaction equation
CC(C)[C:3](O)=[O:4].[CH3:7][NH:8][CH2:9][CH:10]=[O:11].[CH:12]1C=CC=CC=1.[O:18]([CH:25]([C:27]1[S:31][C:30]([N:32]=[C:33]=[O:34])=[N:29][N:28]=1)[CH3:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CCCCCC>[O:18]([CH:25]([C:27]1[S:31][C:30]([NH:32][C:33](=[O:34])[N:8]([CH3:7])[CH2:9][CH:10]([O:4][CH3:3])[O:11][CH3:12])=[N:29][N:28]=1)[CH3:26])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 23463592Methylaminoacetaldehyde dimethylacetateHCID 542400035-(1-Phenoxyethyl)-1,3,4-thiadiazol-2-yl isocyanate

Product 1

HCID 233309973-[5-(1-Phenoxyethyl)-1,3,4-thiadiazol-2-yl]-1-methyl-1-(2,2-dimethoxyethyl)urea

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

During a 40 minute period, and at temperatures starting from 25° C. and ending at 47° C., 69.15 grams (0.580 mole) of methylaminoacetaldehyde dimethylacetate was added dropwise to a 300 ml benzene solution containing 143.3 g. (0.580 mole) of the 5-(1-phenoxyethyl)-1,3,4-thiadiazol-2-yl isocyanate isomer (prepared above) and the resulting solution was refluxed for 15 minutes to form a yellow solution. Hexane (1000 ml) was added and the resulting solution was heated on a steam bath, and then seeded with a few crystals of previously purified product. Upon cooling and standing overnight white crystals formed which were filtered, washed with hexane, air dried and then vacuum dried at 50° C. to give 171.4 grams of a powder of 3-[5-(1-phenoxyethyl)-1,3,4-thiadiazol-2-yl]-1-methyl-1-(2,2-dimethoxyethyl) urea. Melting point 117°-121° C.

Workup

  1. customstarting from 25° C.
  2. customending at 47° C.
  3. additioncontaining 143.3 g
  4. temperaturethe resulting solution was refluxed for 15 minutes
  5. customto form a yellow solution
  6. temperaturethe resulting solution was heated on a steam bath
  7. temperatureUpon cooling
  8. waitstanding overnight
  9. customwhite crystals formed which
  10. filtrationwere filtered
  11. washwashed with hexane, air
  12. customdried
  13. customvacuum dried at 50° C.

Sources & evidence

ORD record
ord-d18fe6fafc7648f5850ce455db774f9f
Source dataset
uspto-grants-1980_11
Patent number
US04233057

Reaction notes

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