Water → HCID 18427786, compound

HRID 2305769Notes

Reaction equation

HRID 2305769 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-992bddaa9f4b4f68ad714c09783e9f50
Source dataset
uspto-grants-2002_08
Patent number
US06441018B2

Reaction notes

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