Acetonitrile → HCID 178487887, compound
Reaction equation
[C:1](#[N:3])[CH3:2].C(=O)=O.CC(O)C.[Li]CCCC.CN(/[CH:19]=[N:20]/[C:21]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:22]=1[C:23]([O:25]C)=O)C>C1COCC1.C(O)(=O)C>[OH:25][C:23]1[C:22]2[C:21](=[CH:30][CH:29]=[C:28]([O:31][CH3:32])[CH:27]=2)[N:20]=[CH:19][C:2]=1[C:1]#[N:3]Participants
7
Conditions
- Temperature
- -72 °C
Procedure
To a cold solution of acetonitrile (2 mL, 38 mmol, 2.8 eq) in THF (30 mL) at −72° C. (Dry-ice/IPA) was added dropwise nBuLi (12 mL, 30 mmol, 2.2 eq) under argon atmosphere. The reaction mixture became an orange suspension after 1 h. A solution of methyl 2-{[(1E)-(dimethylamino)methylidene]amino}-5-(methyloxy)benzoate (3.2 g, 13.6 mmol, 1 eq) in THF (30 mL) was then added dropwise while the internal temperature was maintained at −72° C. The resulting mixture was slowly warmed to RT overnight. To the resulting light-brown suspension was added glacial acetic acid (6 mL) with slight cooling. After stirring for 1 h, the suspension was then quenched with water (60 mL) and filtered to give the titled compound (2.3 g, 85% yield).
Workup
- customafter 1 h
- temperatureThe resulting mixture was slowly warmed to RT overnight
- customthe suspension was then quenched with water (60 mL)
- filtrationfiltered
Sources & evidence
- ORD record
- ord-94978249b62c40058da8e719f6de3ca8
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07691850B2
Reaction notes
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