Dimethylformamide → HCID 88308980, compound

HRID 1737220Notes

Reaction equation

HRID 1737220 reaction equation
[CH3:1][N:2](C)[CH:3]=[O:4].OC[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]1[C:18]([O:19][CH3:20])=[N:17][N:16]([CH3:21])[C:15]1=[O:22].C(=O)([O-])[O-:24].[K+].[K+].ClC1[N:31]=[N+:32]([O-])[C:33]2[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[CH:36]C=2N=1>O>[CH3:20][O:19][C:18]1[N:14]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:4][C:3]2[N:31]=[N:32][C:33]3[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[CH:36][C:1]=3[N:2]=2)[C:15](=[O:22])[N:16]([CH3:21])[N+:17]=1[O-:24]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 21841970HCID 21841970, compoundHCID 21841981HCID 21841981, compound

Product 1

HCID 88308980HCID 88308980, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 25 mL of N,N-dimethylformamide containing 0.11 g of the title compound of Step D under a nitrogen atmosphere was added 0.17 g of potassium carbonate and 0.11 g of 3-chloro-7-methoxy-1,2,4-benzotriazine 1-oxide. The reaction mixture was stirred at room temperature for approximately 24 h, and was then poured into water and extracted with dichloromethane. The organic extracts were washed with water and saturated aqueous sodium chloride. The organic layer was dried over magnesium sulfate, filtered and the filtrate was then evaporated to obtain a yellow oil. The yellow oil was crystallized from 1-chlorobutane/hexane to yield 0.11 g of the title compound of Step E, a compound of the invention, as a yellow solid melting at 191-192° C. 1H NMR (400 MHz, CDCl3): δ 3.250 (s,3H), 3.827 (s,3H), 3.964 (s,3H), 7.4-7.52 (m,5H), 7.65 (d,1H), 7.723 (d,1H).

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic extracts were washed with water and saturated aqueous sodium chloride
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe filtrate was then evaporated
  6. customto obtain a yellow oil
  7. customThe yellow oil was crystallized from 1-chlorobutane/hexane

Sources & evidence

ORD record
ord-5e8267c8c51b47cb9302aa41399b025e
Source dataset
uspto-grants-1999_10
Patent number
US05962436

Reaction notes

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