Dimethyl Sulfate → HCID 70456170, compound

HRID 280619Notes

Reaction equation

HRID 280619 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([CH2:17][C:18]1[NH:19][CH:20]=[CH:21][N:22]=1)=[C:11]2[CH3:23])=[O:7])[CH3:4].S(OC)(O[CH3:28])(=O)=O>CN(C)C=O>[CH2:3]([O:5][C:6]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH3:28])[C:12]([CH2:17][C:18]1[NH:22][CH:21]=[CH:20][N:19]=1)=[C:11]2[CH3:23])=[O:7])[CH3:4]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 70457000HCID 70457000, compound

Product 1

HCID 70456170HCID 70456170, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (0.11 g of 50% dispersion in mineral oil) was added portionwise to a stirred solution of 2-[1-imidazolylmethyl]-3-methylindole-5-carboxylic acid ethyl ester (0.57 g) in dry N,N-dimethylformamide (20 ml) and the mixture was stirred at room temperature for 30 minutes. A solution of dimethyl sulphate (0.26 g) in dry N,N-dimethyl-formamide (2.5 ml) was added dropwise and the mixture was stirred at room temperature for 18 hours and then evaporated. The residue was chromatographed on silica gel. Elution with chloroform first gave mineral oil and impurity followed by pure product. Evaporation of the product-containing fractions gave a solid which was crystallised froml ethyl acetate/petrol (b.p. 60°-80°) to give 1,3-dimethyl-2-[1-imidazolylmethyl]indole-5-carboxylic acid ethyl ester (0.40 g), m.p. 109°-110°.

Workup

  1. stirringthe mixture was stirred at room temperature for 18 hours
  2. customevaporated
  3. customThe residue was chromatographed on silica gel
  4. washElution with chloroform first gave mineral oil and impurity
  5. customEvaporation of the product-containing fractions
  6. customgave a solid which
  7. customwas crystallised froml ethyl acetate/petrol (b.p. 60°-80°)

Sources & evidence

ORD record
ord-d8b58c8c9e60434a9e28f2fb819b5405
Source dataset
uspto-grants-1986_05
Patent number
US04590200

Reaction notes

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