Hydrochloric Acid → HCID 57440613, compound

HRID 1011445Notes

Reaction equation

HRID 1011445 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[NH:11][C:12](=O)OC(C)(C)C)=O.CO/C=[CH:22]/[C:23]([O:25][CH3:26])=[O:24].Cl.C([O-])([O-])=O.[Na+].[Na+]>CO>[CH3:10][O:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]2[C:4]=1[N:11]=[CH:12][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:1]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 5323651Methyl 3-methoxyacrylateHCID 10705884(2-FORMYL-6-METHOXY-PHENYL)-CARBAMIC ACID TERT-BUTYL ESTER

Product 1

HCID 57440613HCID 57440613, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl N-(2-formyl-6-methoxyphenyl)carbamate (2.85 g, 11.35 mmol) [described in Org. Lett. 2002, 4(1), 39-42] and methyl trans-3-methoxyacrylate (2.70 mL, 24.96 mmol) dissolved in 60 ml of methanol, was added slowly 40 mL of an aqueous solution of hydrochloric acid 3M. The resulting mixture was stirred under reflux for 3 hours. The reaction mixture was then cooled to room temperature and neutralised by adding Na2CO3. The aqueous solution was extracted with CH2Cl2 (4×70 mL). The combined organic layers were dried over MgSO4, filtered and evaporated under vacuum giving 2.12 g of compound of molecular formula C12H11NO3. The crude product was used without further purification in the next stage. Aspect: orange powder.

Workup

  1. temperatureunder reflux for 3 hours
  2. extractionThe aqueous solution was extracted with CH2Cl2 (4×70 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-085351e4ea504d6f946189d58ef4809a
Source dataset
uspto-grants-2011_07
Patent number
US07977354B2

Reaction notes

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