Thionyl Chloride → N-(beta-chloroethyl)-N-methyl-N'-(2-t-butyl-1,3,4-thiadiazol-5-yl)urea

HRID 1287177Notes

Reaction equation

HRID 1287177 reaction equation
O[CH2:2][CH2:3][N:4]([CH3:17])[C:5]([NH:7][C:8]1[S:12][C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[N:10][N:9]=1)=[O:6].S(Cl)([Cl:20])=O>C1C=CC=CC=1>[Cl:20][CH2:2][CH2:3][N:4]([CH3:17])[C:5]([NH:7][C:8]1[S:12][C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[N:10][N:9]=1)=[O:6]

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 21507110N-(beta-hydroxyethyl)-N-methyl-N'-(2-t-butyl-1,3,4-thiadiazol-5-yl)urea

Product 1

HCID 21507109N-(beta-chloroethyl)-N-methyl-N'-(2-t-butyl-1,3,4-thiadiazol-5-yl)urea

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

The N-(β-hydroxyethyl)-N-methyl-N'-(2-t-butyl-1,3,4-thiadiazol-5-yl)urea prepared in Example 2, thionyl chloride (5 ml) and benzene (100 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture was heated at reflux, with stirring, for a period of about one hour. After this time the benzene and unreacted thionyl chloride were stripped from the reaction mixture under reduced pressure to yield the desired product N-(β-chloroethyl)-N-methyl-N'-(2-t-butyl-1,3,4-thiadiazol-5-yl)urea as the residue.

Workup

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

Sources & evidence

ORD record
ord-a46ea050e4724a8d9728297b1251d5ca
Source dataset
uspto-grants-1976_10
Patent number
US03984228

Reaction notes

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