1,3,4-Thiadiazol-2-amine → 2-{3-(2-Chloroethyl)-3-nitrosoureido}-1,3,4-thiadiazole

HRID 1156405Notes

Reaction equation

HRID 1156405 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[N:5][N:6]=1.[Cl:7][CH2:8][CH2:9][N:10]([N:16]=[O:17])[C:11](N=[N+]=[N-])=[O:12]>N1C=CC=CC=1>[Cl:7][CH2:8][CH2:9][N:10]([N:16]=[O:17])[C:11](=[O:12])[NH:1][C:2]1[S:3][CH:4]=[N:5][N:6]=1

Participants

4

Reactant 2

HCID 199091,3,4-Thiadiazol-2-amineHCID 10654895N-(2-chloroethyl)-N-nitrosocarbamoylazide

Product 1

HCID 130029522-{3-(2-Chloroethyl)-3-nitrosoureido}-1,3,4-thiadiazoleYield 76.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Ten grams of 2-amino-1,3,4-thiadiazole was dissolved in 100 ml of pyridine, and cooled with ice. While stirring the solution, 26.5 g of N-(2-chloroethyl)-N-nitrosocarbamoyl azide was gradually added, and after the addition, the stirring was continued for 60 minutes. The reaction solution was poured into ice water, and the precipitated crystals were washed with water, dried and recrystallized from methanol, to obtain 17.8 g (Yield 75%) of 2-{3-(2-chloroethyl)-3-nitrosoureido}-1,3,4-thiadiazole. The physical properties of this compound were identical with those of the compound obtained by Example 1.

Workup

  1. temperaturecooled with ice
  2. additionwas gradually added
  3. additionafter the addition
  4. washthe precipitated crystals were washed with water
  5. customdried
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-9b38d1c485114ce5ade8676781ede09e
Source dataset
uspto-grants-1982_06
Patent number
US04335247

Reaction notes

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