Ammonia → HCID 14330445, compound

HRID 981676Notes

Reaction equation

HRID 981676 reaction equation
C([O:4][C:5]1[C:10]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:9]([S:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:8]=[CH:7][CH:6]=1)(=O)C.N>C(O)C>[OH:4][C:5]1[C:10]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:9]([S:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 14330444HCID 14330444, compound

Product 1

HCID 14330445HCID 14330445, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 6-acetoxy-2-(ethoxycarbonylmethylthio)-phenylacetate (132 g) is added at room temperature to a solution of ammonia (34 g) in anhydrous ethanol (1.0 L). After standing for 2 hours the solvent is evaporated in vacuo and the residue is mixed with methylene chloride and 1 N hydrochloric acid. The layers are separated and the organic layer is washed with water to neutrality, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated in vacuo to obtain (as shown by NMR) ethyl 6-hydroxy-2-(ethoxycarbonylmethylthio)-phenylacetate as an oil.

Workup

  1. customthe solvent is evaporated in vacuo
  2. additionthe residue is mixed with methylene chloride and 1 N hydrochloric acid
  3. customThe layers are separated
  4. washthe organic layer is washed with water to neutrality
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-2dcdd3efc259474faef417ef1882f784
Source dataset
uspto-grants-1991_02
Patent number
US04992465

Reaction notes

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