2-Chloroethanol → HCID 59601968, compound

HRID 1799225Notes

Reaction equation

HRID 1799225 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH3:12])=[CH:6][CH:5]=1.[CH2:14](Cl)[CH2:15]O.C(N(C(C)C)CC)(C)C.[OH2:27]>C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH2:14][CH3:15])[CH2:11][CH2:12][OH:27])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 342-ChloroethanolHCID 962WaterHCID 81531DiisopropylethylamineHCID 11805323HCID 11805323, compound

Product 1

HCID 59601968HCID 59601968, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 15 g (84 mmol) of 4-(ethylamino)benzoic acid methyl ester, 15 mL (0.224 mol) of ethylene chlorohydrine and 14.5 mL (84 mmol) of diisopropyl ethyl amine was refluxed for 5 hours. During the reflux, the temperature rose from 105° C. to 140° C. The reaction mixture was allowed to cool down to room temperature and 100 mL of water and 250 mL of ethyl acetate was added. After extraction, the organic fraction was isolated, washed 3 times with 50 mL of water, once with 50 mL of brine and dried over MgSO4. The solvent was removed under reduced pressure and N-ethyl-N-(2-hydroxyethyl)-4-aminobenzoic acid methyl ester was isolated by preparative column chromatography on Kieselgel 60 (Aldrich) using cyclohexane/ethyl acetate 1/1 as eluent. 5.0 g of N-ethyl-N-(2-hydroxyethyl)-4-aminobenzoic acid methyl ester was isolated (m.p. 61-64° C.)

Workup

  1. temperaturewas refluxed for 5 hours
  2. customrose from 105° C. to 140° C
  3. extractionAfter extraction
  4. customthe organic fraction was isolated
  5. washwashed 3 times with 50 mL of water
  6. dry with materialonce with 50 mL of brine and dried over MgSO4
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-27debc10cbfd4379a2b90e6d962b6628
Source dataset
uspto-grants-2013_01
Patent number
US08344038B2

Reaction notes

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