Hydrochloric Acid → 2-(2-Mesylamino-1,3-thiazol-4-yl)glyoxylic acid

HRID 1902714Notes

Reaction equation

HRID 1902714 reaction equation
[S:1]([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[O:17])[C:12]([O:14]CC)=[O:13])[N:10]=1)([CH3:4])(=[O:3])=[O:2].[OH-].[Na+].Cl>O>[S:1]([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[O:17])[C:12]([OH:14])=[O:13])[N:10]=1)([CH3:4])(=[O:2])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19978726Ethyl 2-(2-mesylamino-1,3-thiazol-4-yl)glyoxylate

Product 1

HCID 199787632-(2-Mesylamino-1,3-thiazol-4-yl)glyoxylic acidYield 81.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 2-(2-mesylamino-1,3-thiazol-4-yl)glyoxylate (13.9 g.) was added with stirring at ambient temperature to a solution of sodium hydroxide (5.0 g.) in water (150 ml.). The mixture was stirred for 1 hour at ambient temperature, adjusted to pH 7 with conc. hydrochloric acid and washed with ethyl acetate. The aqueous layer was adjusted to pH 0.5 with conc. hydrochloric acid to precipitate yellow crystals. The crystals were collected by filtration, washed with water and dried to give 2-(2-mesylamino-1,3-thiazol-4-yl)glyoxylic acid (10.16 g.).

Workup

  1. washwashed with ethyl acetate
  2. customto precipitate yellow crystals
  3. filtrationThe crystals were collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-280e5604ecc64151b2cec9c355439bbb
Source dataset
uspto-grants-1982_12
Patent number
US04364943

Reaction notes

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