Hydrochloric Acid → 5-Amino-2-chloro-4-fluorophenylthioacetic acid

HRID 247765Notes

Reaction equation

HRID 247765 reaction equation
C([NH:4][C:5]1[C:6]([F:16])=[CH:7][C:8]([Cl:15])=[C:9]([CH2:11][C:12]([OH:14])=[S:13])[CH:10]=1)(=O)C.Cl.[OH-].[Na+]>>[NH2:4][C:5]1[C:6]([F:16])=[CH:7][C:8]([Cl:15])=[C:9]([CH2:11][C:12]([OH:14])=[S:13])[CH:10]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 1784742305-(N-acetylamino)-2-chloro-4-fluorophenylthioacetic acid

Product 1

HCID 1785076495-Amino-2-chloro-4-fluorophenylthioacetic acidYield 73%

Procedure

A suspension of 5-(N-acetylamino)-2-chloro-4-fluorophenylthioacetic acid (89.8 g) in a 10 % aqueous hydrochloric acid solution was refluxed for 2 hours under heating. After being allowed to cool, an aqueous solution of sodium hydroxide was added to make the suspension at pH 4. After ice-cooling, the precipitated crystals were collected by filteration, washed with ice-water and dried to give 55.0 g of 5-amino-2-chloro-4-fluorophenylthioacetic acid.

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperatureunder heating
  3. temperatureto cool
  4. temperatureAfter ice-cooling
  5. customthe precipitated crystals were collected by filteration
  6. washwashed with ice-water
  7. customdried

Sources & evidence

ORD record
ord-e2579107b82b45db98887b867b173eaf
Source dataset
uspto-grants-1987_11
Patent number
US04709049

Reaction notes

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