Toluene → HCID 18629193, compound

HRID 1060572Notes

Reaction equation

HRID 1060572 reaction equation
[Cl:1][C:2]1[C:11](Cl)=[N:10][C:9]2[C:4](=[CH:5][C:6]([N+:14]([O-:16])=[O:15])=[C:7]([F:13])[CH:8]=2)[N:3]=1.[CH3:17][C:18]([CH3:21])([O-:20])[CH3:19].[K+].C1(C)C=CC=CC=1.P([O-])(O)(O)=O.[Na+]>C(O)(C)(C)C>[C:18]([O:20][C:11]1[C:2]([Cl:1])=[N:3][C:4]2[C:9](=[CH:8][C:7]([F:13])=[C:6]([N+:14]([O-:16])=[O:15])[CH:5]=2)[N:10]=1)([CH3:21])([CH3:19])[CH3:17]

Participants

6

Reactant 4

HCID 1140TolueneHCID 10491682HCID 10491682, compoundHCID 23665647Potassium tert-butoxideHCID 23672064Monosodium phosphate

Product 1

HCID 18629193HCID 18629193, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of 2,3-dichloro-6-fluoro-7-nitroquinoxaline 5.24 g in tetrahydrofran (50 mL), was added dropwise a solution of potassium tert-butoxide 2.51 g in tert-butanol 60 mL at −10 to −8° C. for about 1 hr. After the addition, the mixture was stirred at 0° C. for 1 hr, to which toluene 100 mL and a solution of 0.1M sodium dihydrogen phosphate 20 mL were added, then which was poured into a separatory funnel. The organic layer was washed with water and saturated saline, dried over MgSO4, and evaporated under reduced pressure. The residue was purified with silica gel column (120 g, toluene:hexane=1:1), to give the title compound (pale yellow crystal) 4.19 g.

Workup

  1. additionAfter the addition
  2. additionwhich was poured into a separatory funnel
  3. washThe organic layer was washed with water and saturated saline
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure
  6. customThe residue was purified with silica gel column (120 g, toluene:hexane=1:1)

Sources & evidence

ORD record
ord-34be72745c2a4bdea19b3430a0f9b363
Source dataset
uspto-grants-2003_02
Patent number
US06525054B1

Reaction notes

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