Thionyl Chloride → 6-Amino-7-chloro-benzo[1,2,5]thiadiazole-5-carboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([NH2:11])=[C:6]([Cl:12])[C:5]=1[NH2:13].C(N(CC)C(C)C)(C)C.[S:24](Cl)(Cl)=O>C(#N)C>[CH3:1][O:2][C:3]([C:4]1[C:5]([NH2:13])=[C:6]([Cl:12])[C:7]2[C:8]([CH:9]=1)=[N:10][S:24][N:11]=2)=[O:14]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a suspension of 20 mg (93 mmol) of 2,4,5-triamino-3-chloro-benzoic acid methyl ester in 1 ml of acetonitrile, is added 32 ml (0.19 mmol) of N,N-diisopropylethylamine followed by 9 ml (0.13 mmol) of thionyl chloride. The mixture is stirred at 80° C. over the night. Then, 32 ml of N,N-diisopropylethylamine is added again as well as 9 ml of thionyl chloride and the mixture is again stirred for 5 hours at a temperature of 80° C. The solvent is evaporated and the residue is suspended in EtOAc. After filtration, EtOAc is evaporated and 18 mg (73.9 mmol, 80%) of a yellowish-brown solid is obtained. LC/MS: 244/246 (M+1)+.
Workup
- stirringthe mixture is again stirred for 5 hours at a temperature of 80° C
- customThe solvent is evaporated
- filtrationAfter filtration, EtOAc
- customis evaporated
Sources & evidence
- ORD record
- ord-734552580aa149b5aee55e8bbe3ac6f7
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08580785B2
Reaction notes
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