Toluene → 4-chloro-N-ethylbenzothiazolone

HRID 847810Notes

Reaction equation

HRID 847810 reaction equation
[Cl:1][C:2]1[C:7]2[N:8]=[CH:9][S:10](=[O:11])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[C:14]1(C)C=CC=C[CH:15]=1.S(OCC)(OCC)(=O)=O>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[C:7]2[N:8]([CH2:14][CH3:15])[CH2:9][S:10](=[O:11])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 6163Diethyl SulfateHCID 14798Sodium HydroxideHCID 534006884-Chlorobenzothiazolone

Product 1

HCID 704500904-chloro-N-ethylbenzothiazoloneYield 98.1%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

4-Chlorobenzothiazolone (4.64 g, 0.025 mole) was dissolved in a solution of sodium hydroxide (1.60 g, 0.0375 mole) in water (100 c.c.), and tetra-n-butylammonium bromide (0.24 g, 7.5×10-4 mole) and toluene (40 c.c.) were added thereto. Diethyl sulfate (5.78 g, 0.0375 mole) was added dropwise thereto at room temperature, and the mixture was stirred at room temperature for 1 hour, followed by phase-separation. The toluene layer was washed once with water, and the solvent was removed under reduced pressure to obtain 5.24 g of 4-chloro-N-ethylbenzothiazolone as white crystals. Yield 98.1%, purity 98.5%, m.p. 96°-98.5° C.

Workup

  1. additionwere added
  2. customfollowed by phase-separation
  3. washThe toluene layer was washed once with water
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-167ca29a49014f95b13dc47e81cbd232
Source dataset
uspto-grants-1981_10
Patent number
US04293702

Reaction notes

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