Acetic Acid → HCID 19752333, compound

HRID 483341Notes

Reaction equation

HRID 483341 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[N:21]=[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][N:23]4[C:28]=3[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:16][CH:15]=2)[C:7]([CH:11]=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].[C-]#N.[Na+].[C:37](O)(=[O:39])[CH3:38]>C(O)C.[O-2].[O-2].[Mn+4]>[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]3[N:21]=[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][N:23]4[C:28]=3[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:18][CH:19]=2)[C:7]([C:11]([O:39][CH2:37][CH3:38])=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8929Sodium CyanideHCID 14989464HCID 14989464, compound

Product 1

HCID 19752333HCID 19752333, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 702EthanolSolvent

Procedure

0.28 g (0.6 mmol) of compound A from Example 1d) is dissolved in 5 ml of ethanol. 0.15 g of sodium cyanide is added followed by 53 μl of glacial acetic acid and 1.25 g of manganese dioxide. Stirring at RT for 32 h is followed by filtration with suction, washing with ethanol and concentration of the filtrate. After taking up in H2O, the pH is adjusted to 3-4 with 2% HCl, and extraction with CH2Cl2 is carried out. The organic phase is dried with Na2SO4 and then concentrated. The crude product is reacted without further purification.

Workup

  1. filtrationis followed by filtration with suction
  2. washwashing with ethanol and concentration of the filtrate
  3. extractionthe pH is adjusted to 3-4 with 2% HCl, and extraction with CH2Cl2
  4. dry with materialThe organic phase is dried with Na2SO4
  5. concentrationconcentrated
  6. customThe crude product is reacted without further purification

Sources & evidence

ORD record
ord-c6aef684ccc64727947381c06dcb3abf
Source dataset
uspto-grants-1993_07
Patent number
US05225414

Reaction notes

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