Water → HCID 86643546, compound

HRID 453568Notes

Reaction equation

HRID 453568 reaction equation
[CH:1]([C:3]1[S:7][C:6]([CH3:8])=[C:5]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:4]=1)=O.[H-].[Na+].CI.O.CN(C)[CH:27]=[O:28]>>[CH:27]([C:6]1[S:7][C:3]([CH3:1])=[C:4]([CH2:5][NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:8]=1)=[O:28]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59411381HCID 59411381, compound

Product 1

HCID 86643546HCID 86643546, compoundYield 43%

Procedure

To a solution of benzyl (5-formyl-2-methyl-3-thienyl)carbamate (1.6 g) in N,N-dimethylformamide (20 mL) was slowly added sodium hydride (60%, oily, 0.3 g) at 0° C., and the mixture was stirred at room temperature for 30 min. Methyl iodide (0.47 mL) was added to the reaction mixture, and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography to give benzyl (5-formyl-2-methyl-3-thienyl)methylcarbamate (0.72 g, yield 43%) as a yellow oil from a fraction eluted with ethyl acetate-hexane (1:3, volume ratio).

Workup

  1. customat 0° C.
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cfe8d8ece6da476885b6406bda4192c1
Source dataset
uspto-grants-2013_07
Patent number
US08492405B2

Reaction notes

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