2-(Methylamino)ethanol → N-(beta-hydroxyethyl)-N-methyl-N'-(2-t-butyl-1,3,4-thiadiazol-5-yl)urea

HRID 1287176Notes

Reaction equation

HRID 1287176 reaction equation
[C:1]([C:5]1[S:6][C:7]([N:10]=[C:11]=[O:12])=[N:8][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:13][NH:14][CH2:15][CH2:16][OH:17]>C(OCC)(=O)C>[OH:17][CH2:16][CH2:15][N:14]([CH3:13])[C:11]([NH:10][C:7]1[S:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[N:9][N:8]=1)=[O:12]

Participants

4

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 64524562-t-Butyl-1,3,4-thiadiazol-5-yl Isocyanate

Product 1

HCID 21507110N-(beta-hydroxyethyl)-N-methyl-N'-(2-t-butyl-1,3,4-thiadiazol-5-yl)urea

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-t-Butyl-1,3,4-thiadiazol-5-yl isocyanate dimer (10 grams), N-methyl-N-β-hydroxyethylamine (4.4 grams) and ethyl acetate (50 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer, reflux condenser and thermometer. The reaction mixture was heated at reflux with stirring for a period of about 2 hours. After this time the reaction mixture was stripped of solvent under reduced pressure to yield the desired product N-(β-hydroxyethyl)-N-methyl-N'-(2-t-butyl-1,3,4-thiadiazol-5-yl)urea as an oily residue.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux

Sources & evidence

ORD record
ord-a522f4f5125b4f38a55a456224681f06
Source dataset
uspto-grants-1976_10
Patent number
US03984228

Reaction notes

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