Dimethylformamide → HCID 19349406, compound

HRID 2107770Notes

Reaction equation

HRID 2107770 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:5]=[C:6]([C:16]([CH3:20])([CH3:19])[C:17]#[N:18])[CH:7]=[C:8]([CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)[CH:9]=1.S([O-])([O-])(=O)=O.[CH3:26][S:27]C(N)=[NH2+].CSC(N)=[NH2+].[OH-].[Na+].CN(C)C=O>O>[CH3:19][C:16]([C:6]1[CH:7]=[C:8]([CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)[CH:9]=[C:4]([CH2:3][S:27][CH3:26])[CH:5]=1)([CH3:20])[C:17]#[N:18]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 6604939S-methyl isothiourea hemisulfateHCID 19349446HCID 19349446, compound

Product 1

HCID 19349406HCID 19349406, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the product from Example 28 (0.6 g), S-methylthiouronium sulphate (0.56 g), 10N aqueous sodium hydroxide (1 ml) and dimethylformamide (5 ml) was stirred at room temperature for 18 h, diluted with water (20 ml) and extracted twice with dichloromethane. The extracts were combined, dried and evaporated to dryness under reduced pressure, and the residue was purified by flash column chromatography, eluting with methanol:ethyl acetate (1:49 by volume) to give 2-methyl-2-[3-methylthiomethyl-5-(1H-1,2,4-triazol-1-ylmethyl)phenyl]-propiononitrile. Nmr in deuteriochloroform: δ 8.12(1H,s), 8.0(1H,s), 7.4(1H,m), 7.27(1H,m), 7.15(1H,m), 5.38(2H,s), 3.66(2H,s), 2.0(3H,s), 1.72(6H,s).

Workup

  1. extractionextracted twice with dichloromethane
  2. customdried
  3. customevaporated to dryness under reduced pressure
  4. customthe residue was purified by flash column chromatography
  5. washeluting with methanol:ethyl acetate (1:49 by volume)

Sources & evidence

ORD record
ord-2e838140041a4217a6b83fe8aece84d4
Source dataset
uspto-grants-1990_06
Patent number
US04935437

Reaction notes

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