Ammonia → HCID 14330445, compound

HRID 2292156Notes

Reaction equation

HRID 2292156 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 (1.0L). After standing for 2 hours the solvent is evaporated in vacuo and the residue is mixed with methylene chloride and 1N 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 1N 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-ba4a610f65c34b9e925684f634d724f7
Source dataset
uspto-grants-1989_01
Patent number
US04801605

Reaction notes

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