Ethanol → HCID 13097103, compound

HRID 1164530Notes

Reaction equation

HRID 1164530 reaction equation
C(O)C.[Cl-].[NH4+].[O:6]=[C:7]1[N:11]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]2[CH:18]=[C:19]([Cl:25])[C:20]([N+:22]([O-])=O)=[CH:21][C:9]=2[S:8]1>[Fe].O>[O:6]=[C:7]1[N:11]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]2[CH:18]=[C:19]([Cl:25])[C:20]([NH2:22])=[CH:21][C:9]=2[S:8]1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 13097106HCID 13097106, compound

Product 1

HCID 13097103HCID 13097103, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

To a mixture of ethanol (10 liters) and water (1 liter) were added ammonium chloride (25 g) and iron metal (300 g). To the mixture was added ethyl 2-oxo-5-chloro-6-nitro-3-benzothiazolineacetate (434.6 g) under mild reflux. After refluxing with stirring for 4 hours, the resultant mixture was filtered under warm condition. The filter cake was washed with ethanol. The combined filtrate and washings were concentrated under reduced pressure and cooled to ambient temperature to give crystals, which were separated by filtration to give crystalline ethyl 2-oxo-5-chloro-6-amino-3-benzothiazolineacetate (347.8 g).

Workup

  1. temperatureAfter refluxing
  2. filtrationthe resultant mixture was filtered
  3. temperatureunder warm condition
  4. washThe filter cake was washed with ethanol
  5. concentrationThe combined filtrate and washings were concentrated under reduced pressure
  6. customto give crystals, which
  7. customwere separated by filtration

Sources & evidence

ORD record
ord-db896b32085845bb90fb61ab4944185f
Source dataset
uspto-grants-1983_01
Patent number
US04370340

Reaction notes

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