Water → HCID 21852285, compound

HRID 617435Notes

Reaction equation

HRID 617435 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:10]=[C:8]([OH:9])[C:7]([OH:11])=[C:6]([N+:12]([O-:14])=[O:13])[CH:5]=1.O.[C:16]1(C)C=CC=CC=1>CS(C)=O.CN1CCCC1=O.C(Cl)Cl>[Cl:3][C:4]1[CH:5]=[C:6]([N+:12]([O-:14])=[O:13])[C:7]2[O:11][CH2:16][O:9][C:8]=2[CH:10]=1

Participants

8

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 14798Sodium HydroxideHCID 21852281HCID 21852281, compound

Product 1

HCID 21852285HCID 21852285, compoundYield 70.3%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

Under N2 8.0 g of NaOH (powdered) is dissolved in 80 ml of DMSO, or, alternatively, in N-methylpyrrolidone (NMP) at 80° C. In about 15 min a solution of 20.0 g of 5-chloro-3-nitro-catechol in 20 ml DMSO (NMP) and 100 ml CH2Cl2 is added at 80° C. The reaction mixture is heated at 130° C. for 8-30 hours while stirring. After cooling down to room temp., successively 200 ml water and 400 ml toluene are added. Stirring for 5 min., separation of the layers, and extraction of the water layer with 100 ml toluene yields a combined organic phase, which is washed twice with 50 ml satd. aqueous NaCl solution, with 50 ml water and twice with 100 ml satd. aqueous NaCl solution. After evaporation of the solvent (100 mbar, 40° C.), the desired product is obtained in a yield of 70.3%; purity 84%.

Workup

  1. customat 80° C
  2. temperatureAfter cooling down to room temp.
  3. stirringStirring for 5 min.
  4. customseparation of the layers, and extraction of the water layer with 100 ml toluene
  5. customyields a combined organic phase, which
  6. washis washed twice with 50 ml
  7. customAfter evaporation of the solvent (100 mbar, 40° C.)

Sources & evidence

ORD record
ord-4f5a4f9539344d5790489037603d6470
Source dataset
uspto-grants-1999_09
Patent number
US05948909

Reaction notes

Loading…