Dimethylcarbamoyl Chloride → 1,1,3-Trimethyl-3-[5-(beta-chloro-alpha,alpha-dimethylethyl)-1,3,4-thiadiazol-2-yl]urea

HRID 839765Notes

Reaction equation

HRID 839765 reaction equation
[CH3:1][NH:2][C:3]1[S:4][C:5]([C:8]([CH3:12])([CH3:11])[CH2:9][Cl:10])=[N:6][N:7]=1.[CH3:13][N:14]([CH3:18])[C:15](Cl)=[O:16]>N1C=CC=CC=1>[CH3:13][N:14]([CH3:18])[C:15]([N:2]([CH3:1])[C:3]1[S:4][C:5]([C:8]([CH3:11])([CH3:12])[CH2:9][Cl:10])=[N:6][N:7]=1)=[O:16]

Participants

4

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 127696565-(1-Chloro-2-methylpropan-2-yl)-N-methyl-1,3,4-thiadiazol-2-amine

Product 1

HCID 203216611,1,3-Trimethyl-3-[5-(beta-chloro-alpha,alpha-dimethylethyl)-1,3,4-thiadiazol-2-yl]ureaYield 89.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 50.0 g of 2-methylamino-5-(β-chloro-α,α-dimethylethyl)-1,3,4-thiadiazole in 300 ml of pyridine was added 46.0 g of dimethyl carbamyl chloride and the reaction heated at reflux temperature for 16 hrs. After cooling, the pyridine was removed on the rotary evaporator and water added to the residue. The reaction was extracted with ether which was shaken with water, saturated sodium chloride and dried over Na2SO4. The solvent was removed at reduced pressure giving 60 g of a viscous oil. Crystallization was effected using a mixture of ether-petroleum ether; wt. 34.5 g (52%), m.p. 80°-82°. Recrystallization from ether-petroleum ether gave the analytical sample, m.p. 82°-83°.

Workup

  1. temperaturethe reaction heated
  2. temperatureat reflux temperature for 16 hrs
  3. temperatureAfter cooling
  4. customthe pyridine was removed on the rotary evaporator and water
  5. additionadded to the residue
  6. extractionThe reaction was extracted with ether which
  7. dry with materialdried over Na2SO4
  8. customThe solvent was removed at reduced pressure

Sources & evidence

ORD record
ord-7a63a30b2b5345deabd7801f8db4600b
Source dataset
uspto-grants-1978_06
Patent number
US04097264

Reaction notes

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