Tetrahydrofuran → Ethyl n-carbobenzoxy-4-amino-3,5-dimethylbenzoate

HRID 411277Notes

Reaction equation

HRID 411277 reaction equation
[NH2:1][C:2]1[C:12]([CH3:13])=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[CH3:14].O1CCCC1.[H-].[Na+].[C:22](Cl)([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>O>[C:22]([NH:1][C:2]1[C:3]([CH3:14])=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][C:12]=1[CH3:13])([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10387Benzyl chloroformateHCID 24758Sodium hydrideHCID 201013Benzoic acid, 4-amino-3,5-dimethyl-, ethyl ester

Product 1

HCID 10639914Ethyl n-carbobenzoxy-4-amino-3,5-dimethylbenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 4-amino-3,5-dimethylbenzoate (2.0 g) was added to a tetrahydrofuran (THF) suspension of sodium hydride (0.82 g) in a nitrogen atmosphere and the mixture was stirred at room temperature for 30 min. Subsequently, carbobenzoxychloride (4.4 ml) was added to the suspension and the mixture was stirred overnight. A small amount of water was added to the reaction solution and the mixture was poured into ice water, followed by extraction with ethyl acetate. Following washing and drying (with magnesium sulfate), the solvent was distilled off under vacuum. The resulting crystal was recovered by filtration in the presence of ethanol and dried under vacuum to yield the end product (3.2 g).

Workup

  1. stirringthe mixture was stirred overnight
  2. extractionfollowed by extraction with ethyl acetate
  3. washFollowing washing
  4. dry with materialdrying (with magnesium sulfate)
  5. distillationthe solvent was distilled off under vacuum
  6. filtrationThe resulting crystal was recovered by filtration in the presence of ethanol
  7. customdried under vacuum

Sources & evidence

ORD record
ord-313c6e3d1c8e4c9794916d90bc6432b6
Source dataset
uspto-grants-2003_05
Patent number
US06559149B1

Reaction notes

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