Trimethyl orthoformate → HCID 57526964, compound

HRID 1452583Notes

Reaction equation

HRID 1452583 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH:15]=[C:14](C=O)[N:13]=[CH:12]1.[CH:18](OC)([O:21][CH3:22])[O:19][CH3:20].C(=O)([O-])[O-].[Na+].[Na+]>CO.O.S([O-])(O)(=O)=O.[Na+]>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH:15]=[C:14]([CH:18]([O:21][CH3:22])[O:19][CH3:20])[N:13]=[CH:12]1

Participants

7

Reactant 3

HCID 9005Trimethyl orthoformateHCID 10340Sodium CarbonateHCID 57527008HCID 57527008, compound2×

Product 1

HCID 57526964HCID 57526964, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 516919Sodium BisulfateCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

1-(2-Fluoro-4-nitrophenyl)-1H-imidazole-4-carboxaldehyde (Intermediate 30) (361.7 g, 1.538 mol) was suspended in dry methanol (1700 ml). Trimethyl orthoformate (340 g, 2 mol) and sodium hydrogen sulfate (8 g) were added and the mixture was heated to reflux for 3.5 hours. It was cooled to room temperature, a solution of sodium carbonate in water (10%, 200 ml) was added and it was stirred for 1 hour. It was diluted with water (4 L) and left for 2 hours. The precipitate was collected by filtration, washed with water and dried to give the title compound (402.4 g) as a solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3.5 hours
  3. waitleft for 2 hours
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-3c8fe5509d2145d2b890ae5ecf908379
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

Loading…