Benzene → HCID 12799743, compound

HRID 1446948Notes

Reaction equation

HRID 1446948 reaction equation
[CH3:1][O:2][CH:3]([O:7][CH3:8])[CH2:4][NH:5][CH3:6].C1C=CC=CC=1.[CH3:15][O:16][CH:17]([C:19]1[S:23][C:22]([N:24]=[C:25]=[O:26])=[N:21][N:20]=1)[CH3:18].CCCCCC>C(OCC)C>[CH3:15][O:16][CH:17]([C:19]1[S:23][C:22]([NH:24][C:25](=[O:26])[N:5]([CH3:6])[CH2:4][CH:3]([O:7][CH3:8])[O:2][CH3:1])=[N:21][N:20]=1)[CH3:18]

Participants

6

Reactant 4

HCID 241BenzeneHCID 8058HexaneHCID 85032,2-DimethoxyethylmethylamineHCID 12799742HCID 12799742, compound

Product 1

HCID 12799743HCID 12799743, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

At ambient temperatures, 5.4 grams (0.045 mole) of methylaminoacetaldehyde dimethylacetal was slowly added to a 50 milliliter benzene solution containing 8.4 grams (0.045 equivalents) of the 5-(1-methoxyethyl)-1,3,4-thiadiazol-2-yl isocyanate dimer (prepared above). The resulting solution was refluxed for 20 minutes; hexane was added resulting in the formation of an oil, the mixture was topped on a roto-vac at 70° C. to 13.2 grams of a hazy viscous oil which was dissolved in diethylether, and filtered. The diethylether solution was topped on a roto-vac at 70° C. to yield 12.9 grams of a red oil of 3-[5-(1-methoxyethyl)-1,3,4-thiadiazol-2-yl]-1-methyl-1-(2,2-dimethoxyethyl)urea.

Workup

  1. additioncontaining
  2. temperatureThe resulting solution was refluxed for 20 minutes
  3. customresulting in the formation of an oil
  4. filtrationfiltered
  5. customwas topped on a roto-vac at 70° C.

Sources & evidence

ORD record
ord-059a4bcc948c4f78a644c14703476fc8
Source dataset
uspto-grants-1982_02
Patent number
US04314842

Reaction notes

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