Ethyl orthoformate → HCID 67081546, compound

HRID 2216927Notes

Reaction equation

HRID 2216927 reaction equation
[CH3:1][O:2][C:3]([N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9](=[O:16])[CH2:8][C:7]2[CH:17]=[CH:18][CH:19]=[CH:20][C:6]1=2)=[O:4].C(OCC)(OCC)O[CH2:23][CH3:24]>C(O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:1][O:2][C:3]([N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9]([O:16][CH2:23][CH3:24])=[CH:8][C:7]2[CH:17]=[CH:18][CH:19]=[CH:20][C:6]1=2)=[O:4]

Participants

5

Reactant 2

HCID 31214Ethyl orthoformateHCID 11346171HCID 11346171, compound

Product 1

HCID 67081546HCID 67081546, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 10-oxo-10,11-dihydro-dibenzo[b,f]azepine-5-carboxylic acid methyl ester (15 g, 56 mmol) in ethanol (75 ml) is heated to 60° C. and a catalytic amount of p-toluene sulfonic acid (0.213 g, 1.1 mmol) is added. After addition of triethyl ortho-formate (8.73 g, 58.9 mmol) the solution is stirred at 60–70° C. for 4 hours. During this reaction the product precipitates as white crystals. The mixture is cooled to room temperature, filtered and dried to yield 16.0 g of pure title compound (97%).

Workup

  1. customDuring this reaction the product
  2. customprecipitates as white crystals
  3. temperatureThe mixture is cooled to room temperature
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-6a325c4262a9402c847f5b7f5eae02c4
Source dataset
uspto-grants-2006_09
Patent number
US07112673B2

Reaction notes

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