2-(Dimethylamino)ethanol → HCID 19611079, compound

HRID 1602323Notes

Reaction equation

HRID 1602323 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH2:6][CH2:7][OH:8])[CH3:5].[CH3:9][O:10][C:11]1[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[CH:24][C:12]=1[C:13]([NH:15][C:16]1[S:17][CH:18]=[C:19]([C:21](O)=[O:22])[N:20]=1)=[O:14]>CN(C)C=O>[CH3:9][O:10][C:11]1[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[CH:24][C:12]=1[C:13]([NH:15][C:16]1[S:17][CH:18]=[C:19]([C:21]([O:8][CH2:7][CH2:6][N:4]([CH3:5])[CH3:3])=[O:22])[N:20]=1)=[O:14]

Participants

5

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 24758Sodium hydrideHCID 19611008HCID 19611008, compound

Product 1

HCID 19611079HCID 19611079, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In 10 ml of N,N-dimethylformamide, 278 mg of sodium hydride was suspended. To the resulting suspension, 620 mg of N,N-dimethylaminoethanol was added dropwise, followed by stirring at room temperature for one hour. In another 10 ml portion of N,N-dimethylformamide, 1.57 g of 2-[N-(2,4,5-trimethoxybenzoyl)amino]-4-(hydroxycarbonyl)-1,3-thiazole was suspended. To the resulting suspension, 827 mg of carbonyl diimiazole was added, followed by stirring at room temperature for one hour. Two reaction mixtures so obtained were combined and were stirred at 100° C. for one hour. The reaction mixture was poured into an ice water and the crystals so precipitated were collected by filtration. The crystals so obtained were recrystallized from isopropyl alcohol, whereby 1.4 g of the title compound was obtained. Yield: 74%.

Workup

  1. stirringby stirring at room temperature for one hour
  2. customTwo reaction mixtures
  3. customso obtained
  4. stirringwere stirred at 100° C. for one hour
  5. customthe crystals so precipitated
  6. filtrationwere collected by filtration
  7. customThe crystals so obtained
  8. customwere recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-ed7171b9aff74c36af83907656955515
Source dataset
uspto-grants-1999_11
Patent number
US05981557

Reaction notes

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