Ethylene Glycol → HCID 10465944, compound

HRID 359776Notes

Reaction equation

HRID 359776 reaction equation
C(O)CO.[OH-].[K+].NC1[S:9][C:10]2[CH:16]=[C:15]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:14]=[CH:13][C:11]=2[N:12]=1.C1(C)C=CC=CC=1>O.C(O)(=O)C>[NH2:12][C:11]1[CH:13]=[CH:14][C:15]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:16][C:10]=1[SH:9]

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 1140TolueneHCID 14797Potassium HydroxideHCID 23449966-Phenoxybenzo[d]thiazol-2-amine

Product 1

HCID 10465944HCID 10465944, compoundYield 101.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

14 ml of ethylene glycol were added to a solution of 42.3 g of caustic potash dissolved in 49 ml of water, and after the air in the reaction vessel had been replaced by nitrogen, 10.57 g of 2-amino-6-phenoxybenzothiazole were added. While blowing nitrogen through the reaction mixture, the reaction was carried out on an oil bath at 135° C. for 2 hours. At the end of this time, the reaction mixture was cooled, 105 ml of toluene were added, and the mixture was ,neutralized by the addition of 42.3 mI of acetic acid. The toluene layer was separated, and the aqueous layer was once again extracted with toluene. The combined toluene extracts were washed with an aqueous solution of sodium bicarbonate, with water, and with an aqueous solution of sodium chloride, in that order, after which they were dried over anhydrous magnesium sulfate. The resulting solution was then concentrated by evaporation under reduced pressure, and the residue Was dried, to give 9.6 g of the title compound as a solid. This compound was used for the next reaction without further purification.

Workup

  1. additionwere added
  2. temperatureAt the end of this time, the reaction mixture was cooled
  3. customThe toluene layer was separated
  4. extractionthe aqueous layer was once again extracted with toluene
  5. washThe combined toluene extracts were washed with an aqueous solution of sodium bicarbonate, with water
  6. dry with materialwith an aqueous solution of sodium chloride, in that order, after which they were dried over anhydrous magnesium sulfate
  7. concentrationThe resulting solution was then concentrated by evaporation under reduced pressure
  8. customthe residue Was dried

Sources & evidence

ORD record
ord-45ea703c96c44866819f9228d23f2709
Source dataset
uspto-grants-1991_03
Patent number
US05002942

Reaction notes

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