Hydrochloric Acid → HCID 12437435, compound

HRID 388417Notes

Reaction equation

HRID 388417 reaction equation
C[O:2][C:3]([C:5]1[C:6]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[N:7][S:8][C:9]=1[C:10]([O:12]C)=[O:11])=[O:4].[OH-].[Na+].Cl>O>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([C:6]2[C:5]([C:3]([OH:4])=[O:2])=[C:9]([C:10]([OH:12])=[O:11])[S:8][N:7]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12437415HCID 12437415, compound

Product 1

HCID 12437435HCID 12437435, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 4.4 g of 5 and 2.8 g of NaOH in 20 ml of water is kept at reflux for 2.5 h. The reaction mixture is cooled, diluted with water (150 ml) and acidified with conc. HCl (aq). A precipitate forms. The water layer is extracted with EtOAc (2×200 ml; the precipitate slowly dissolves). The combined organic layers are washed with brine and dried (Na2SO4). Concentration afforded 3.9 grams of 6 as a white solid.

Workup

  1. temperatureat reflux for 2.5 h
  2. temperatureThe reaction mixture is cooled
  3. extractionThe water layer is extracted with EtOAc (2×200 ml
  4. dissolutionthe precipitate slowly dissolves)
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationConcentration

Sources & evidence

ORD record
ord-27a95c169a004e85a82cbd44d907a720
Source dataset
uspto-grants-2013_02
Patent number
US08377953B2

Reaction notes

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