Water → HCID 18427786, compound

HRID 727393Notes

Reaction equation

HRID 727393 reaction equation
[Cl:1][C:2]1[CH:35]=[CH:34][CH:33]=[CH:32][C:3]=1[C:4]([C:6]1[C:7]([OH:31])=[N:8][N:9]([C:22]2[C:27]([Cl:28])=[CH:26][C:25]([Cl:29])=[CH:24][C:23]=2[Cl:30])[C:10]=1[N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21])=[O:5].[H-].[Na+].S(OCC)(O[CH2:42][CH3:43])(=O)=O.O>CS(C)=O>[Cl:1][C:2]1[CH:35]=[CH:34][CH:33]=[CH:32][C:3]=1[C:4]([C:6]1[C:7]([O:31][CH2:42][CH3:43])=[N:8][N:9]([C:22]2[C:23]([Cl:30])=[CH:24][C:25]([Cl:29])=[CH:26][C:27]=2[Cl:28])[C:10]=1[N:11]1[C:12](=[O:21])[C:13]2=[CH:20][CH:19]=[CH:18][CH:17]=[C:14]2[C:15]1=[O:16])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6163Diethyl SulfateHCID 24758Sodium hydrideHCID 178519521HCID 178519521, compound

Product 1

HCID 18427786HCID 18427786, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 0.55 g (1.0 mmol) of the compound of Step C in 10 mL of dry dimethyl sulfoxide was treated portionwise with 36 mg (1.5 mmol) of sodium hydride and the resulting mixture was stirred for 30 minutes at room temperature. Then 0.21 mL (0.25 g, 1.61 mmol) of diethyl sulfate was added and the reaction mixture was stirred for one hour at room temperature. The reaction mixture was poured into water and the product was extracted into ethyl acetate. The extracts were washed with water and dried with brine and magnesium sulfate, and evaporated to a gum. The product was crystallized from boiling ethanol to give the product (230 mg, 40%) as fine crystals, m.p. 215°-216° C.

Workup

  1. stirringthe reaction mixture was stirred for one hour at room temperature
  2. extractionthe product was extracted into ethyl acetate
  3. washThe extracts were washed with water
  4. dry with materialdried with brine and magnesium sulfate
  5. customevaporated to a gum
  6. customThe product was crystallized

Sources & evidence

ORD record
ord-d00793db9ed641bd9bf06d49ec2df548
Source dataset
uspto-grants-1998_01
Patent number
US05712303

Reaction notes

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