1,3-Dioxolane-2-methanamine, N-methyl- → N-(2-trifluoromethyl-1,3,4-thiadiazol-5-yl)-N'-(1,3-dioxolan-2-ylmethyl)-N'-methylurea

HRID 1605796Notes

Reaction equation

HRID 1605796 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[S:4][C:5]([N:8]=[C:9]=[O:10])=[N:6][N:7]=1.[O:13]1[CH2:17][CH2:16][O:15][CH:14]1[CH2:18][NH:19][CH3:20]>C1C=CC=CC=1>[F:12][C:2]([F:11])([F:1])[C:3]1[S:4][C:5]([NH:8][C:9]([N:19]([CH2:18][CH:14]2[O:15][CH2:16][CH2:17][O:13]2)[CH3:20])=[O:10])=[N:6][N:7]=1

Participants

4

Reactant 2

HCID 5417541,3-Dioxolane-2-methanamine, N-methyl-HCID 131418952-Isocyanato-5-(trifluoromethyl)-1,3,4-thiadiazole

Product 1

HCID 21544990N-(2-trifluoromethyl-1,3,4-thiadiazol-5-yl)-N'-(1,3-dioxolan-2-ylmethyl)-N'-methylurea

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-Trifluoromethyl-1,3,4-thiadiazol-5-yl isocyanate dimer (3.1 grams) was added to a solution of N-(1,3-dioxolan-2-ylmethyl)-N-methylamine (2grams) in benzene (10 ml) contained in a glass reaction vessel equipped with a mechanical stirrer and thermometer. The mixture was heated on a steam bath for a period of about 1 hour. The mixture was then stripped of solvent under reduced pressure to yield a solid residue. The residue was recrystallized from an ether-pentane mixture to yield the desired product N-(2-trifluoromethyl-1,3,4-thiadiazol-5-yl)-N'-(1,3-dioxolan-2-ylmethyl)-N'-methylurea having a melting point of 114° to 115°C.

Workup

  1. customcontained in a glass reaction vessel
  2. customequipped with a mechanical stirrer
  3. temperatureThe mixture was heated on a steam bath for a period of about 1 hour
  4. customto yield a solid residue
  5. customThe residue was recrystallized from an ether-pentane mixture

Sources & evidence

ORD record
ord-f797ef40af9d4d5a8eb4bce37f37af52
Source dataset
uspto-grants-1976_04
Patent number
US03951640

Reaction notes

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