Water → HCID 54402024, compound

HRID 2256914Notes

Reaction equation

HRID 2256914 reaction equation
[CH3:1][C:2]([SH:5])([CH3:4])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[Cl:12][C:13]1[CH:23]=[C:22]([N+]([O-])=O)[CH:21]=[CH:20][C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16].O>CC(C)=O>[Cl:12][C:13]1[CH:23]=[C:22]([S:5][C:2]([CH3:4])([CH3:3])[CH3:1])[CH:21]=[CH:20][C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6387tert-Butyl mercaptan4×HCID 11430Potassium Carbonate2×HCID 12654166HCID 12654166, compound

Product 1

HCID 54402024HCID 54402024, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Methyl-2-propanethiol (7.47 g) was added to a suspension of potassium carbonate (9.52 g) in acetone. Ethyl 2-chloro-4-nitrobenzoate (10 g) was added and the mixture was stirred at room temperature overnight. Further 2-methyl-2-propanethiol (1.0 g) was added and the mixture was stirred and heated to 30° C. for 1 hour. Further 2-methyl-2-propanethiol (1.0 g) was added and the mixture was stirred and heated at reflux for 0.5 hours. Potassium carbonate (9.52 g) and 2-methyl-2-propanethiol was added and the mixture was stirred and heated at reflux overnight. Water was added and it was extracted with ethyl acetate, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give ethyl 2-chloro-4-(1,1-dimethylethylsulphenyl)benzoate (12.1 g) as a red oil NMR (CDCl3) 1.3 (s,9H) 1.35(t,3H) 4.3(q,2H) 7.1-7.7 (m,3H).

Workup

  1. stirringthe mixture was stirred
  2. temperatureheated to 30° C. for 1 hour
  3. stirringthe mixture was stirred
  4. temperatureheated
  5. temperatureat reflux for 0.5 hours
  6. stirringthe mixture was stirred
  7. temperatureheated
  8. temperatureat reflux overnight
  9. extractionit was extracted with ethyl acetate
  10. washwashed with water
  11. dry with materialdried (MgSO4)
  12. filtrationfiltered
  13. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-ff1acf587dc04388ac01bce910c74a3d
Source dataset
uspto-grants-1997_08
Patent number
US05656573

Reaction notes

Loading…