Hydrochloric Acid → Ethyl alpha-cyano-5-nitro-1,2-benziso-thiazole-3-acetate

HRID 428399Notes

Reaction equation

HRID 428399 reaction equation
[O-]CC.[Na+].[Na].[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])#[N:7].Cl[C:15]1[C:19]2[CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=[CH:23][C:18]=2[S:17][N:16]=1.Cl>C(O)C>[C:6]([CH:8]([C:15]1[C:19]2[CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=[CH:23][C:18]=2[S:17][N:16]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10])#[N:7]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7764Ethyl cyanoacetateHCID 1980981,2-Benzisothiazole, 3-chloro-5-nitro-HCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 12607115Ethyl alpha-cyano-5-nitro-1,2-benziso-thiazole-3-acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A sodium ethoxide solution (previously prepared from ethanol and sodium (1.00 g, 0.0430 mol)) is cooled with an ice-acetone bath, treated portionwise with ethyl cyanoacetate (4.51 g, 0.0398 mol), stirred at room temperature for 30 minutes, treated with 3-chloro-5-nitro-1,2-benzisothiazole (4.27 91 0.0199 mol), stirred at room temperature overnight, cooled to 0° C., and treated dropwise with 10% hydrochloric acid (15.0 mL). The resultant aqueous mixture is stirred at room temperature for one hour and filtered to obtain a solid. The solid is washed with ethanol and air-dried to give the title product as a yellow solid which is identified by NMR spectral analysis.

Workup

  1. temperatureis cooled with an ice-acetone bath
  2. stirringstirred at room temperature overnight
  3. temperaturecooled to 0° C.
  4. stirringThe resultant aqueous mixture is stirred at room temperature for one hour
  5. filtrationfiltered
  6. customto obtain a solid
  7. washThe solid is washed with ethanol
  8. customair-dried

Sources & evidence

ORD record
ord-0ec689fda12a455ab5bbc5712ad5f15c
Source dataset
uspto-grants-2001_11
Patent number
US06313295B1

Reaction notes

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