Azobisisobutyronitrile → 3-(1-Bromoethyl)-5-amino-1,2,4-thiadiazole
Reaction equation
[CH2:1]([C:3]1[N:7]=[C:6]([NH2:8])[S:5][N:4]=1)[CH3:2].C1C(=O)N([Br:16])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:16][CH:1]([C:3]1[N:7]=[C:6]([NH2:8])[S:5][N:4]=1)[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
3-Ethyl-5-amino-1,2,4-thiadiazole, 1.1 eq NBS and a small amount of AIBN were dissolved in CCl4 and refluxed at 80° C. over-night. Standard work up followed by purification on silica gel with DCM as mobile phase gave the 3-(1-bromoethyl)-5-amino-1,2,4-thiadiazole. Subsequently, 0.9 eq of NaI were dissolved in dry acetone and 3-(1-bromoethyl)-5-amino-1,2,4-thiadiazole. 1 eq of Na2CO3 and 1 eq of 3-fluorothiophenol were then added and the reaction was stirred at room temperature over-night. The reaction was quenched with water and worked up and purified using standard procedures.
Workup
- customStandard work up followed by purification on silica gel with DCM as mobile phase
Sources & evidence
- ORD record
- ord-af5aa92b143041b1a1409125a481c094
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07173030B2
Reaction notes
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