Triethylamine → HCID 178514553, compound
Reaction equation
[N:1]([CH2:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][N:6]=1)=[N+:2]=[N-:3].Cl.[NH2:14][OH:15].C(N(CC)CC)C>CO>[OH:15][NH:14][C:9]([C:8]1[CH:7]=[N:6][C:5]([CH2:4][N:1]=[N+:2]=[N-:3])=[CH:12][CH:11]=1)=[NH:10]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
To a solution of the azide of Example 51 (11-3) (6.46 g, 40.6 mmol) in methanol (100 ml) was added hydroxylamine hydrochloride (3.95 g, 56.84 mmol), followed by triethylamine (9.6 ml). The solution was heated to 65° C. for four hours. The solvent was removed under reduced pressure and the remaining residue was extracted with ethylacetate (300 ml) and water (100 ml). The water layer was re-extracted with ethylacetate (2×200 ml). The combined organic extracts were washed with brine (2×100 ml), dried over MgSO4 and evaporated to yield the title product (11-4) (7.8 g).
Workup
- customThe solvent was removed under reduced pressure
- extractionthe remaining residue was extracted with ethylacetate (300 ml) and water (100 ml)
- extractionThe water layer was re-extracted with ethylacetate (2×200 ml)
- washThe combined organic extracts were washed with brine (2×100 ml)
- dry with materialdried over MgSO4
- customevaporated
Sources & evidence
- ORD record
- ord-5bd53f449c444882b95df0f337f1f7a1
- Source dataset
- uspto-grants-2003_07
- Patent number
- US06586405B2
Reaction notes
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