Sulfuric Acid → HCID 140340991, compound

HRID 638142Notes

Reaction equation

HRID 638142 reaction equation
[C:1]([C:4]1[C:5]([OH:18])=[C:6]([Cl:17])[C:7]2[O:11][CH:10](/[C:12](=[N:14]\[OH:15])/[OH:13])[CH2:9][C:8]=2[CH:16]=1)(=[O:3])[CH3:2].O1CC[CH2:21][CH2:20]1.S(=O)(=O)(O)O>C(O)C>[C:1]([C:4]1[C:5]([OH:18])=[C:6]([Cl:17])[C:7]2[O:11][CH:10](/[C:12](=[N:14]\[OH:15])/[O:13][CH2:20][CH3:21])[CH2:9][C:8]=2[CH:16]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8028TetrahydrofuranHCID 178465826HCID 178465826, compound

Product 1

HCID 140340991HCID 140340991, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The acid 4a was esterified by stirring in a solution of tetrahydrofuran, ethanol, and concentrated sulfuric acid (39:60:1) for 16 hours at room temperature. The resulting solution was evaporated and the residue dissolved in ethyl acetate, washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate, and evaporated. Recrystallization from ethyl acetate/hexane furnished 76.1% of white crystals, m.p. 154°-155° C. Anal. (C13H14ClNO5) C,H,N.

Workup

  1. customThe resulting solution was evaporated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with aqueous sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customRecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-a087e1af75bf4fe3b9370c468e44f109
Source dataset
uspto-grants-1985_12
Patent number
US04560558

Reaction notes

Loading…