Benzene → HCID 20289954, compound

HRID 1856101Notes

Reaction equation

HRID 1856101 reaction equation
[CH3:1][O:2][CH:3]([O:7][CH3:8])[CH2:4][NH:5][CH3:6].C1C=CC=CC=1.[CH3:15][C:16]1[CH:32]=[CH:31][C:19]([O:20][CH:21]([C:23]2[S:27][C:26]([N:28]=[C:29]=[O:30])=[N:25][N:24]=2)[CH3:22])=[CH:18][CH:17]=1>C1C=CC=CC=1.CCCCCC>[CH3:15][C:16]1[CH:17]=[CH:18][C:19]([O:20][CH:21]([C:23]2[S:27][C:26]([NH:28][C:29](=[O:30])[N:5]([CH3:6])[CH2:4][CH:3]([O:7][CH3:8])[O:2][CH3:1])=[N:25][N:24]=2)[CH3:22])=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 85032,2-DimethoxyethylmethylamineHCID 53680789HCID 53680789, compound

Product 1

HCID 20289954HCID 20289954, compound

Reagents, catalysts & solvents 1

HCID 110624Benzene hexaneSolvent

Procedure

Methylaminoacetaldehyde dimethylacetal (1.8 grams, 0.015 mole) was added to a benzene solution containing 4.0 grams (0.015 mole) of the 5-[1-(4-methylphenoxy)ethyl]-1,3,4-thiadiazol-2-yl isocyanate dimer (prepared above). The resulting solution was refluxed for 20 minutes, topped on a roto-vac at 70° C. to form a viscous red-orange oil, which was redissolved in benzene-hexane mixture and left to stand overnight. Crystals formed which were removed by suction filtration, and dried in a vacuum oven at 70° C. to 3.2 grams of tan crystals of [5-[1-(4-methylphenoxy)ethyl]-1,3,4-thiadiazol-2-yl]-1-methyl-1-(2,2-dimethoxyethyl)urea, (melting point 94°-100° C.).

Workup

  1. additioncontaining
  2. temperatureThe resulting solution was refluxed for 20 minutes
  3. customtopped on a roto-vac at 70° C.
  4. customto form a viscous red-orange oil, which
  5. waitleft
  6. customCrystals formed which
  7. customwere removed by suction filtration
  8. dry with materialdried in a vacuum oven at 70° C. to 3.2 grams of tan crystals of [5-[1-(4-methylphenoxy)ethyl]-1,3,4-thiadiazol-2-yl]-1-methyl-1-(2,2-dimethoxyethyl)urea, (melting point 94°-100° C.)

Sources & evidence

ORD record
ord-800d684c71b24034bb444c746668597a
Source dataset
uspto-grants-1980_08
Patent number
US04218236

Reaction notes

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