HCID 53705050, compound → HCID 2825090, compound

HRID 2097634Notes

Reaction equation

HRID 2097634 reaction equation
[N+:1](=[C:3]([C:8](=O)[CH2:9][O:10][CH3:11])[C:4]([O:6][CH3:7])=[O:5])=[N-:2].[NH4+]=[S:14]>>[CH3:11][O:10][CH2:9][C:8]1[S:14][N:2]=[N:1][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

2

Reactant 1

HCID 53705050HCID 53705050, compound

Product 1

HCID 2825090HCID 2825090, compoundYield 85.8%

Procedure

Methyl 2-diazo-4-methoxy-3-oxobutanoate (4.5 g, 0.026 mol) was cooled in an ice bath and ammonium sulfide (8.0 g, 0.12 mol) (40-48%) was added drop-wise over 2 minutes. White precipitate formed. The slurry was stirred for 30 minutes, and then purified by flash chromatography to give the desired product (4.2 g, 85%) as a light oil, that crystallized readily upon standing. 1H NMR (400 MHz, CD3OD): δ 5.02 (s, 2H), 3.98 (s, 3H), 3.57 (s, 3H). MF═C6H8N2O3S; LCMS calculated for C6H9N2O3S(M+H)+: m/z=189.0.

Workup

  1. customWhite precipitate
  2. customformed
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-cb06f24e8f3e41c2a03977ddec1392f7
Source dataset
uspto-grants-2013_05
Patent number
US08450351B2

Reaction notes

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