Dimethylformamide → HCID 19349406, compound

HRID 1636808Notes

Reaction equation

HRID 1636808 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-58a5af4b64364dfeb6e570146fd8e21d
Source dataset
uspto-grants-2000_03
Patent number
USRE036617

Reaction notes

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