Dimethylformamide → 2-(2-Propen-1-ylthio)pyrazine

HRID 2257523Notes

Reaction equation

HRID 2257523 reaction equation
[CH2:1](O)[CH:2]=[CH2:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.BrN1C(=O)CCC1=O.CN(C)C=O.[SH:37][C:38]1[CH:43]=[N:42][CH:41]=[CH:40][N:39]=1>ClCCl.C(N(CC)CC)C.O>[CH2:1]([S:37][C:38]1[CH:43]=[N:42][CH:41]=[CH:40][N:39]=1)[CH:2]=[CH2:3]

Participants

9

Reactant 5

HCID 6228DimethylformamideHCID 7858Allyl AlcoholHCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 178527737HCID 178527737, compound

Product 1

HCID 30258992-(2-Propen-1-ylthio)pyrazineYield 44.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

0.58 g of allyl alcohol was dissolved in 50 ml of dichloromethan and 2.89 g of triphenylphosphine and 1.96 g of N-bromosuccinimide were added thereto. The mixture was stirred at room temperature for 30 minutes, and 5 ml of dimethylformamide solution in which 1.0 g of 2-mercaptopyrazine and 1 ml of triethylamine were dissolved was added to the above solution. The resulting mixture was stirred at room temperature for 1 hour and poured into 100 ml of water. The organic layer was separated and concentrated to dryness. The residues were purified by silica gel chromatography using ethyl acetate:n-hexane=1:1 as an eluate to give 0.6 g of titled compound.

Workup

  1. additionwas added to the above solution
  2. stirringThe resulting mixture was stirred at room temperature for 1 hour
  3. customThe organic layer was separated
  4. concentrationconcentrated to dryness
  5. customThe residues were purified by silica gel chromatography

Sources & evidence

ORD record
ord-567a66f0b28244a88f5fb2b6b1881f56
Source dataset
uspto-grants-1997_08
Patent number
US05658913

Reaction notes

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