Diethyl Sulfate → HCID 13424429, compound

HRID 462612Notes

Reaction equation

HRID 462612 reaction equation
CN(C)C=O.[H-].[Na+].[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=2[C:19]([OH:21])=[O:20])=[C:12]([CH3:26])[CH:11]=1.S(OCC)(O[CH2:31][CH3:32])(=O)=O>O.C(O)(=O)C.CCOCC>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=2[C:19]([O:21][CH2:31][CH3:32])=[O:20])=[C:12]([CH3:26])[CH:11]=1

Participants

8

Reactant 4

HCID 6163Diethyl SulfateHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 13424434HCID 13424434, compound

Product 1

HCID 13424429HCID 13424429, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Dimethylformamide (250 ml) was added to sodium hydride (obtained from 4.80 g of 50% oil dispersion after washing and drying) and the mixture cooled to 0°-5° C. 2-(4-Methoxy-2-methylphenylamino)benzoic acid (25.7 g) was then added, and the mixture was stirred at room temperature for 45 minutes and then cooled to 0°-5° C. To the latter mixture was added 13 ml of diethyl sulfate, and the reaction mixture was stirred overnight at room temperature and poured into a mixture of ether, acetic acid, water and ice. The mixture was extracted with ether and the ether extracts washed with 1N potassium hydroxide and dried over anhydrous magnesium sulfate. Removal of the ether and crystallization of the residue from isopropyl alcohol gave 12.2 g of ethyl 2-(4-methoxy-2-methylphenylamino)benzoate as a pale yellow solid, m.p. 42°-43° C.

Workup

  1. temperaturethe mixture cooled to 0°-5° C
  2. temperaturecooled to 0°-5° C
  3. stirringthe reaction mixture was stirred overnight at room temperature
  4. extractionThe mixture was extracted with ether
  5. washthe ether extracts washed with 1N potassium hydroxide
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customRemoval of the ether and crystallization of the residue from isopropyl alcohol

Sources & evidence

ORD record
ord-71812991612d48cb8ec6027cbaeb3e49
Source dataset
uspto-grants-1985_05
Patent number
US04515980

Reaction notes

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