2-t-Butyl-1,3,4-thiadiazol-5-yl Isocyanate → N-(2-t-butyl-1,3,4-thiadiazol-5-yl)-N'-(1,3-dioxolan-2-ylmethyl)-N'-ethylurea

HRID 1605799Notes

Reaction equation

HRID 1605799 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].[O:13]1[CH2:17][CH2:16][O:15][CH:14]1[CH2:18][NH:19][CH2:20][CH3:21]>C1C=CC=CC=1>[C:1]([C:5]1[S:6][C:7]([NH:10][C:11]([N:19]([CH2:18][CH:14]2[O:15][CH2:16][CH2:17][O:13]2)[CH2:20][CH3:21])=[O:12])=[N:8][N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 64524562-t-Butyl-1,3,4-thiadiazol-5-yl IsocyanateHCID 13193169N-(1,3-dioxolan-2-yl)methyl ethylamine

Product 1

HCID 21545055N-(2-t-butyl-1,3,4-thiadiazol-5-yl)-N'-(1,3-dioxolan-2-ylmethyl)-N'-ethylurea

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-t-Butyl-1,3,4-thiadiazol-5-yl isocyanate dimer (3grams) and a solution of N-(1,3-dioxolan-2-ylmethyl)-N-ethylamine (2 grams) in benzene (10 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The mixture is warmed on a steam bath with stirring for a period of about 1 hour. After this time the mixture is stripped of solvent under reduced pressure to yield a solid residue. The residue is recrystallized to yield the desired product N-(2-t-butyl-1,3,4-thiadiazol-5-yl) -N'-(1,3-dioxolan-2-ylmethyl)-N'-ethylurea.

Workup

  1. customequipped with a mechanical stirrer
  2. temperatureThe mixture is warmed on a steam bath
  3. customto yield a solid residue
  4. customThe residue is recrystallized

Sources & evidence

ORD record
ord-7d662c32efdf4c21a289cfa18244df10
Source dataset
uspto-grants-1976_04
Patent number
US03951640

Reaction notes

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