Sodium Methoxide → HCID 178491138, compound

HRID 1404856Notes

Reaction equation

HRID 1404856 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6](/[N:10]=[C:11](/[NH:17]/[N:18]=[CH:19]/[C:20]2[CH:25]=[CH:24][C:23]([C:26]3[N:30]=[CH:29][N:28]([C:31]4[CH:36]=[CH:35][C:34]([O:37][C:38]([F:41])([F:40])[F:39])=[CH:33][CH:32]=4)[N:27]=3)=[CH:22][CH:21]=2)\[S:12][CH2:13][C:14]([OH:16])=[O:15])=[C:5]([CH3:42])[CH:4]=1.C[O-].[Na+:45]>C1COCC1>[Na+:45].[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6](/[N:10]=[C:11](/[NH:17]/[N:18]=[CH:19]/[C:20]2[CH:25]=[CH:24][C:23]([C:26]3[N:30]=[CH:29][N:28]([C:31]4[CH:32]=[CH:33][C:34]([O:37][C:38]([F:40])([F:41])[F:39])=[CH:35][CH:36]=4)[N:27]=3)=[CH:22][CH:21]=2)\[S:12][CH2:13][C:14]([O-:16])=[O:15])=[C:5]([CH3:42])[CH:4]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 178491137HCID 178491137, compound

Product 1

HCID 178491138HCID 178491138, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-((Z)-(4-methoxy-2,6-dimethylphenylimino)((E)-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzylidene)hydrazinyl)methylthio)acetic acid (77.7 mg, 0.130 mmol) in THF (10 mL) was added slowly sodium methanolate (0.5 M in methanol; 260 μL, 0.130 mmol) at room temperature. The mixture immediately turned a darker yellow and was then evaporated at room temperature under vacuum giving a light orange solid. This material was triturated with Et2O (2×) and isolated by decanting using a centrifuge and drying under a nitrogen stream and then under high vacuum. The title compound was isolated as a light orange solid (32 mg, 39%): mp 146-154° C.; 1H NMR (400 MHz, methanol-d4) δ 9.11 (s, 1H), 8.64-7.68 (m, 7H), 7.51 (m, 2H), 6.70 (s, 2H), 3.85-3.70 (m, 4H), 3.61 (m, 1H), 2.29 (s, 6H); ESIMS m/z 599 (M+H).

Workup

  1. customwas then evaporated at room temperature under vacuum
  2. customgiving a light orange solid
  3. customThis material was triturated with Et2O (2×)
  4. customisolated
  5. customby decanting
  6. customdrying under a nitrogen stream

Sources & evidence

ORD record
ord-890d393805434017a21472ae018c7cc3
Source dataset
uspto-grants-2014_12
Patent number
US08916183B2

Reaction notes

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