Hydrochloric Acid → HCID 13097099, compound

HRID 1903738Notes

Reaction equation

HRID 1903738 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]2[CH:13]=[C:14]([Cl:18])[C:15](N)=[CH:16][C:4]=2[S:3]1.Cl.N([O-])=O.[Na+].[C:24]([O-])(=O)[CH3:25].[Na+]>O.C1C=CC=CC=1>[O:1]=[C:2]1[N:6]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]2[CH:13]=[C:14]([Cl:18])[C:15]([C:25]3[CH:24]=[CH:13][CH:5]=[CH:4][CH:16]=3)=[CH:16][C:4]=2[S:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 517045Sodium AcetateHCID 13097103HCID 13097103, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 13097099HCID 13097099, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of ethyl 2-oxo-5-chloro-6-amino-3-benzothiazolineacetate (347.8 l g) and conc.hydrochloric acid (1040 ml) was stirred for 30 minutes at ambient temperature. After the resultant mixture was cooled to 2° C., a solution of sodium nitrite (88.3 g) in water (120 ml) was added dropwise thereto below 5° C. in the course of 40 minutes. The mixture was stirred for 20 minutes at 0° C. To the resultant mixture was added benzene (5.2 l) in the course of 30 minutes. After the reaction mixture was stirred for an hour and 40 minutes under ice-cooling, a solution of sodium acetate.3H2O (1.56 kg) in water (3.6 l) was added dropwise thereto under ice-cooling in the course of an hour. The mixture was stirred overnight at ambient temperature. The organic layer was separated, washed with water and dried over anhydrous magnesium sulfate, concentrated under reduced pressure to give a residue, which was recrystallized from ethanol to give ethyl 2-oxo-5-chloro-6-phenyl-3-benzothiazolineacetate (311.5 g).

Workup

  1. custombelow 5° C.
  2. customin the course of 40 minutes
  3. stirringAfter the reaction mixture was stirred for an hour and 40 minutes under ice-
  4. temperaturecooling
  5. temperatureunder ice-cooling in the course of an hour
  6. stirringThe mixture was stirred overnight at ambient temperature
  7. customThe organic layer was separated
  8. washwashed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customto give a residue, which
  12. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-54fbbac523894e60843e2dcbcbeecea1
Source dataset
uspto-grants-1984_03
Patent number
US04438126

Reaction notes

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