HCID 178433051, compound → HCID 22064686, compound

HRID 1828088Notes

Reaction equation

HRID 1828088 reaction equation
[CH3:1][CH:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([CH2:13][OH:14])[NH:3]1>ClCCl.O=[Mn]=O>[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([CH:13]=[O:14])[N:3]=1

Participants

4

Reactant 1

HCID 178433051HCID 178433051, compound

Product 1

HCID 22064686HCID 22064686, compoundYield 34.9%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of (RS)-(5-methyl-1-phenyl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)-methanol (2.28 g) at r.t. in dichloromethane (75 ml) was added MnO2 (8.06 g). The black suspension was heated to reflux and stirring was continued for 24 h. The solids were filtered off and washed with CH2Cl2. The filtrate was concentrated. The crude product was purified by chromatography (silica gel, cyclohexane=>cyclohexane/EtOAc 1:4) to give 5-methyl-1-phenyl-1H-[1,2,4]triazole-3-carbaldehyde (0.78 g) as light yellow solid. MS 188.3 ([M+H]+)

Workup

  1. temperatureThe black suspension was heated
  2. temperatureto reflux
  3. filtrationThe solids were filtered off
  4. washwashed with CH2Cl2
  5. concentrationThe filtrate was concentrated
  6. customThe crude product was purified by chromatography (silica gel, cyclohexane=>cyclohexane/EtOAc 1:4)

Sources & evidence

ORD record
ord-d8a0430744db4628a51e9021fb899e2e
Source dataset
uspto-grants-2006_06
Patent number
US07056932B2

Reaction notes

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