Hydrochloric Acid → HCID 19822300, compound

HRID 1030230Notes

Reaction equation

HRID 1030230 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([NH:11][C:12]2[S:13][CH:14]=[C:15]([CH2:17][C:18]([O:20]CC)=[O:19])[N:16]=2)[CH:8]=[C:7]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:6]=1[OH:27])([CH3:4])([CH3:3])[CH3:2].S(S([O-])=O)([O-])=O.[Na+].[Na+].[OH-].[Na+].Cl>C(O)C.O.C(O)(=O)C>[C:1]([C:5]1[CH:10]=[C:9]([NH:11][C:12]2[S:13][CH:14]=[C:15]([CH2:17][C:18]([OH:20])=[O:19])[N:16]=2)[CH:8]=[C:7]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:6]=1[OH:27])([CH3:3])([CH3:4])[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24489Sodium DithioniteHCID 19822289HCID 19822289, compound

Product 1

HCID 19822300HCID 19822300, compoundYield 67.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2,6-Di-tert-butyl-4-[(4-ethoxycarbonylmethyl-2-thiazolyl)amino]phenol (produced in Example 17) (0.80 g) was dissolved in 30 ml of ethanol, a solution of 2 g of sodium hydrosulfite in 20 ml of water was added and then 15 ml of 2 N aqueous sodium hydroxide was added, and the resultant mixture was stirred at room temperature for 4 hours. The reaction mixture was cooled in an ice bath and, after addition of 15 ml of 2 N hydrochloric acid and further addition of 3 ml of acetic acid, extracted with dichloromethane. The organic layer was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated. The colorless crystals thus obtained were washed with diethyl ether to give 0.50 g of the desired compound.

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe colorless crystals thus obtained
  7. washwere washed with diethyl ether

Sources & evidence

ORD record
ord-af9d999417dd4518a3d35347766cbfa7
Source dataset
uspto-grants-1992_04
Patent number
US05104889

Reaction notes

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