Diethyl Sulfate → HCID 11805323, compound

HRID 1799224Notes

Reaction equation

HRID 1799224 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1.S(OCC)(O[CH2:16][CH3:17])(=O)=O.C(N(C(C)C)CC)(C)C>O>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:16][CH3:17])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6163Diethyl SulfateHCID 12082Methyl 4-aminobenzoateHCID 81531Diisopropylethylamine

Product 1

HCID 11805323HCID 11805323, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 25.0 g (0.165 mol) 4-aminobenzoic acid methyl ester, 21.75 mL (0.165 mol) of diethyl sulfate and 30 mL (0.174 mol) of diisopropyl ethyl amine was heated to 120° C. for 1 hour. The reaction was exothermic and the temperature rose to 140° C. The mixture was allowed to cool down to room temperature and 100 mL of water was added. 4-(ethylamino)benzoic acid methyl ester crystallized over night, was isolated by filtration, washed 3 times with water and dried. The crude 4-(ethylamino)benzoic acid methyl ester was recrystallized from methanol. 14.44 g of 4-(ethylamino)benzoic acid methyl ester was isolated (m.p. 132-135° C.).

Workup

  1. customrose to 140° C
  2. temperatureto cool down to room temperature
  3. custom4-(ethylamino)benzoic acid methyl ester crystallized over night
  4. customwas isolated by filtration
  5. washwashed 3 times with water
  6. customdried
  7. customThe crude 4-(ethylamino)benzoic acid methyl ester was recrystallized from methanol

Sources & evidence

ORD record
ord-3275c7ecc42546649e427562033d1935
Source dataset
uspto-grants-2013_01
Patent number
US08344038B2

Reaction notes

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