Oxalyl chloride → 5-[N-(1-ethylpropyl)aminosulfonyl]-1,3,4-thiadiazol-2-yl isocyanate

HRID 127140Notes

Reaction equation

HRID 127140 reaction equation
[NH2:1][C:2]1[S:3][C:4]([S:7]([NH:10][CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])(=[O:9])=[O:8])=[N:5][N:6]=1.C(Cl)(=O)[C:17](Cl)=[O:18]>C1(C)C(C)=CC=CC=1>[CH2:12]([CH:11]([NH:10][S:7]([C:4]1[S:3][C:2]([N:1]=[C:17]=[O:18])=[N:6][N:5]=1)(=[O:8])=[O:9])[CH2:14][CH3:15])[CH3:13]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 202861092-amino-5-[N-(1-ethylpropyl)aminosulfonyl]-1,3,4-thiadiazole

Product 1

HCID 544460095-[N-(1-ethylpropyl)aminosulfonyl]-1,3,4-thiadiazol-2-yl isocyanate

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2-Amino-5-[N-(1-ethylpropyl)aminosulfonyl]-1,3,4-thiadiazole (0.10 mole) and xylene (200 ml) are charged into a glass reaction vessel fitted with a mechanical stirrer, thermometer and condenser. The mixture is dried by azeotroping off water and is then cooled to room temperature. Oxalyl chloride (0.15 mole) is added; the reaction mixture is warmed to a temperature of from 80° C. to about 100° C. and stirred at this temperature for a period of about 1 hour. The mixture is then heated to reflux and stirred for an additional 2 hours. Solvent is then stripped off leaving the desired product 5-[N-(1-ethylpropyl)aminosulfonyl]-1,3,4-thiadiazol-2-yl isocyanate dimer as the residue.

Workup

  1. customfitted with a mechanical stirrer
  2. customThe mixture is dried
  3. customby azeotroping off water
  4. temperaturethe reaction mixture is warmed to a temperature of from 80° C. to about 100° C.
  5. temperatureThe mixture is then heated
  6. temperatureto reflux
  7. stirringstirred for an additional 2 hours

Sources & evidence

ORD record
ord-84b057d066fd4023813f0b2a8a1a621f
Source dataset
uspto-grants-1981_03
Patent number
US04255182

Reaction notes

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