Ammonia → HCID 68428264, compound
Reaction equation
[C:1]1([N:7]2[CH:11]=[C:10]([Si:12]([CH3:15])([CH3:14])[CH3:13])[NH:9][N:8]2[C:16]([OH:18])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.O[N:21]1C2C=CC=CC=2N=N1.O.N>ClCCl>[C:1]1([N:7]2[CH:11]=[C:10]([Si:12]([CH3:15])([CH3:14])[CH3:13])[NH:9][N:8]2[C:16]([NH2:21])=[O:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
In a nitrogen atmosphere, 630 mg of 3-phenyl-5-trimethylsilanyl-1H-[1,2,3]triazole-2-carboxylic acid which is the compound prepared in the above 2) was dissolved in 5 ml of dichloromethane, 671 mg of 1-hydroxybenzotriazole monohydrate and 907 mg of a water-soluble dichlorohexyl carbodiimide were added thereto, the reaction solution was cooled down to −78° C. and ammonia gas was introduced thereinto followed by stirring for 2 days. Water was added to the reaction solution, the mixture was extracted with ethyl acetate and the ethyl acetate layer washed with a saturated saline solution and dried over sodium sulfate. The solvent was evaporated in vacuo and the residue was separated and purified by a silica gel column chromatography (hexane/ethyl acetate=2/1) to give 550 mg of the title compound as a white solid.
Workup
- customprepared in the above 2)
- extractionthe mixture was extracted with ethyl acetate
- washthe ethyl acetate layer washed with a saturated saline solution
- dry with materialdried over sodium sulfate
- customThe solvent was evaporated in vacuo
- customthe residue was separated
- custompurified by a silica gel column chromatography (hexane/ethyl acetate=2/1)
Sources & evidence
- ORD record
- ord-3f10da82d6604b448952c22e3a43abfe
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07858800B2
Reaction notes
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