Hydrochloric Acid → HCID 18630213, compound

HRID 368661Notes

Reaction equation

HRID 368661 reaction equation
[Cl:1][C:2]1[C:12]([CH:13]=O)=[CH:11][CH:10]=[C:9]([Si:15]([CH3:18])([CH3:17])[CH3:16])[C:3]=1[C:4]([NH:6][CH2:7][CH3:8])=[O:5].[N+:19]([CH3:22])([O-:21])=[O:20].[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[C:12](/[CH:13]=[CH:22]/[N+:19]([O-:21])=[O:20])=[CH:11][CH:10]=[C:9]([Si:15]([CH3:18])([CH3:17])[CH3:16])[C:3]=1[C:4]([NH:6][CH2:7][CH3:8])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 10660666HCID 10660666, compound

Product 1

HCID 18630213HCID 18630213, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the compound of Example 223 (0.199 g, 0.7 mmol) in methanol (5 mL) at 0° C. was added nitromethane (0.3 mL, 5.0 mmol) and 2.5 N NaOH (2.3 mL, 5.8 mmol) portionwise over 2 h. The suspension was dissolved by addition of ice-cold water and cold 2 N HCl (10 mL) was added. The precipitate was filtered and washed with water to afford the crude title compound. The crude product was purified by recrystallization from aq methanol to afford the title compound as a light yellow fluffy solid (60 mg, 26%). m.p. 104-106° C.

Workup

  1. additionwas added
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customto afford the crude title compound
  5. customThe crude product was purified by recrystallization from aq methanol

Sources & evidence

ORD record
ord-a2b367a12445467696f1c1a8b00d6659
Source dataset
uspto-grants-2000_10
Patent number
US06133252

Reaction notes

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