Tert-Butyl nitrite → HCID 25105768, compound

HRID 1199890Notes

Reaction equation

HRID 1199890 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:9]([CH:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][S:12][C:11]2([CH3:21])[CH3:20])[CH:8]=[N:7][C:6]=1N)=[O:4].N(OC(C)(C)C)=O>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[N:9]([CH:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][S:12][C:11]2([CH3:21])[CH3:20])[CH:8]=[N:7][CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 70357084HCID 70357084, compound

Product 1

HCID 25105768HCID 25105768, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5.0 g of 4-amino-1-(3,3-dimethylisothiochroman-4-yl)-5-imidazolecarboxylic acid methyl ester in 10 ml of tetrahydrofuran is added dropwise to a solution of 3.1 ml of tert.-butyl nitrite in 10 ml of tetrahydrofuran. After stirring for 16 hours at room temperature, the reaction mixture is poured onto ice-water. After extraction with ether, the organic phase is washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated by evaporation. The residue is purified by chromatography on silica gel (eluant: ethyl acetate/hexane 2:5). There are thus obtained 3.2 g of 1-(3,3-dimethylisothiochroman-4-yl)-5-imidazolecarboxylic acid methyl ester in the form of a yellow resin which is caused to crystallise with hexane. The crystalline compound has a melting point of 108°-109° C.

Workup

  1. additionthe reaction mixture is poured onto ice-water
  2. extractionAfter extraction with ether
  3. washthe organic phase is washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. customThe residue is purified by chromatography on silica gel (eluant: ethyl acetate/hexane 2:5)
  8. customto crystallise with hexane

Sources & evidence

ORD record
ord-65f5d99304b443cfb8287f268f092010
Source dataset
uspto-grants-1990_02
Patent number
US04904300

Reaction notes

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