Chlorosuccinimide → 2-Amino-5-Chloro-alpha-(Methoxyimino)-4-Thiazoleacetic Acid

HRID 253048Notes

Reaction equation

HRID 253048 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:11][O:12][CH3:13])[C:8]([OH:10])=[O:9])[N:6]=1.[Cl:14]N1C(=O)CCC1=O>C(O)(=O)C>[NH2:1][C:2]1[S:3][C:4]([Cl:14])=[C:5]([C:7](=[N:11][O:12][CH3:13])[C:8]([OH:10])=[O:9])[N:6]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 1252162-(2-Aminothiazole-4-yl)-2-methoxyiminoacetic acid

Product 1

HCID 540093662-Amino-5-Chloro-alpha-(Methoxyimino)-4-Thiazoleacetic Acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

To 500 mL of acetic acid were added 40.0 g (0.20 mol) of 2-amino-α-(methoxyimino)-4-thiazoleacetic acid (Aldrich Chemical Company, Milwaukee, Wis.) and 27.9 g (0.21 mol) N-chlorosuccinimide. The mixture was heated in a 70° C. bath. The solids dissolved within 30 minutes, and after 45 minutes the reaction was complete by MS. The dark solution was allowed to cool to room temperature and concentrated under vacuum to give a dark solid, which was used without purification.

Workup

  1. dissolutionThe solids dissolved within 30 minutes
  2. temperatureto cool to room temperature
  3. concentrationconcentrated under vacuum
  4. customto give a dark solid, which
  5. customwas used without purification

Sources & evidence

ORD record
ord-c9e1f5ca1aa447e3a92137d13921a8f8
Source dataset
uspto-grants-2011_01
Patent number
US07871997B2

Reaction notes

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