Sodium Methoxide → HCID 67167138, compound

HRID 2093784Notes

Reaction equation

HRID 2093784 reaction equation
[CH3:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([CH3:13])=[CH:6][C:3]=1[CH:4]=[O:5].C1(C)C(S([CH2:23][N+:24]#[C-:25])(=O)=O)=CC=CC=1.C[O-].[Na+]>CO>[CH3:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([CH3:13])=[CH:6][C:3]=1[C:4]1[O:5][CH:25]=[N:24][CH:23]=1

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 53627694Toluenesulfonylmethyl isocyanideHCID 86653320HCID 86653320, compound

Product 1

HCID 67167138HCID 67167138, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 2,5-dimethyl-4-nitrobenzaldehyde (75 mg, 0.42 mmol) and toluenesulfonylmethyl isocyanide (TOSMIC) (98 mg, 0.5 mmol) in methanol (2 mL), was added sodium methoxide (68 mg, 1.26 mmol). The mixture was sealed and heated at 90° C. for 15 hr. The reaction mixture was concentrated and partitioned between water and ethyl acetate. The organic layer was separated, dried over sodium sulfate and concentrated. The 5-(2,5-Dimethyl-4-nitrophenyl)oxazole obtained was used in the next step without purification.

Workup

  1. customThe mixture was sealed
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between water and ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-83707cd5f09c41d2accdd36502c8b574
Source dataset
uspto-grants-2013_05
Patent number
US08445505B2

Reaction notes

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