Chloral → N-benzothiazol-6-yl-2-hydroxyimino-acetamide

HRID 1700139Notes

Reaction equation

HRID 1700139 reaction equation
S([O-])([O-])(=O)=O.[Na+].[Na+].[NH2:8][C:9]1[CH:17]=[CH:16][C:12]2[N:13]=[CH:14][S:15][C:11]=2[CH:10]=1.[O:18]=[CH:19][C:20](Cl)(Cl)Cl.Cl.[OH:25][NH2:26]>Cl.C(O)C.O>[S:15]1[C:11]2[CH:10]=[C:9]([NH:8][C:19](=[O:18])[CH:20]=[N:26][OH:25])[CH:17]=[CH:16][C:12]=2[N:13]=[CH:14]1

Participants

8

Reactant 4

HCID 6407ChloralHCID 24436Sodium SulfateHCID 682886-AminobenzothiazoleHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 85408681N-benzothiazol-6-yl-2-hydroxyimino-acetamideYield 94%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a 1-L flask was added a magnetic stir bar, 85 g of sodium sulfate, and 100 mL of water. The mixture was magnetically stirred until all the solids were dissolved. To the resultant aqueous solution was added a solution of 6-aminobenzothiazole (4.96 g, 33.0 mmol) in 50 mL of 1N aqueous hydrochloric acid and 10 mL of ethanol. The mixture was stirred, and chloral (6.0 g, (36 mmol) was added. To the resultant solution was added a solution of hydroxyl amine hydrochloride (7.50 g, 108 mmol) in 30 mL of water. The final mixture was heated with stirring to a gentle boil until all solids dissappeared, and heating was continued for an additional 15 min. The flask was removed from the heat, and the solution was poured onto 500 g of ice. The mixture was stirred as the product precipatated from solution. The precipatate was collected by suction filtration, washed thoroughly with water, filtered, and air dried to provide 6.9 g (94%) of N-benzothiazol-6-yl-2-hydroxyimino-acetamide:

Workup

  1. additionTo a 1-L flask was added a magnetic stir bar
  2. dissolutionwere dissolved
  3. stirringThe mixture was stirred
  4. stirringwith stirring to a gentle boil until all solids
  5. temperatureheating
  6. customThe flask was removed from the heat
  7. additionthe solution was poured onto 500 g of ice
  8. stirringThe mixture was stirred as the product
  9. filtrationThe precipatate was collected by suction filtration
  10. washwashed thoroughly with water
  11. filtrationfiltered
  12. customair dried

Sources & evidence

ORD record
ord-c3e54f51ebf449f4af60cefe95a195b9
Source dataset
uspto-grants-2002_02
Patent number
US06350747B1

Reaction notes

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