Acetic Acid → HCID 68183006, compound

HRID 513700Notes

Reaction equation

HRID 513700 reaction equation
[CH3:1][C:2]([OH:4])=[O:3].[F:5][C:6]1C=[CH:12][C:11]([CH:14]2[C:27]3[CH:26]=[CH:25][C:24]4[C:19](=[N:20][CH:21]=[CH:22][CH:23]=4)[C:18]=3[NH:17][S:16](=[O:29])(=[O:28])[N:15]2[CH3:30])=[CH:10][C:7]=1C=O.[C-:31]#N.[Na+]>CO.O=[Mn]=O>[CH3:31][O:3][C:2](=[O:4])[C:1]1[CH:12]=[C:11]([CH:14]2[C:27]3[CH:26]=[CH:25][C:24]4[C:19](=[N:20][CH:21]=[CH:22][CH:23]=4)[C:18]=3[NH:17][S:16](=[O:28])(=[O:29])[N:15]2[CH3:30])[CH:10]=[CH:7][C:6]=1[F:5]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8929Sodium CyanideHCID 88861907HCID 88861907, compound

Product 1

HCID 68183006HCID 68183006, compoundYield 95.8%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 887MethanolSolvent

Procedure

AcOH (23.1 μl, 0.4 mmol) was added dropwise to a solution of 2-fluoro-5-(2-methyl-3,3-dioxo-1,2,3,4-tetrahydro-3λ*6*-thia-2,4,5-triaza-phenanthren-1-yl)-benzaldehyde 422 (50 mg, 0.13 mmol), MnO2 (176 mg, 2.02 mmol), and sodium cyanide (66 mg, 1.35 mmol) in MeOH (10 ml). The mixture was stirred at room temperature for 3 h. The mixture was filtered and the filtrate was diluted with water (10 ml). The mixture was extracted with EtOAc (15 ml, ×2) and DCM (15 ml). The combined organic phases were concentrated in vacuo to give the title compound (50 mg, 93%) which was used in the next step without further purification.

Workup

  1. filtrationThe mixture was filtered
  2. additionthe filtrate was diluted with water (10 ml)
  3. extractionThe mixture was extracted with EtOAc (15 ml, ×2) and DCM (15 ml)
  4. concentrationThe combined organic phases were concentrated in vacuo

Sources & evidence

ORD record
ord-c217a41f16ba4ae1bf7069879f4deb9b
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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