Dimethyl Sulfoxide → HCID 54249399, compound

HRID 2107774Notes

Reaction equation

HRID 2107774 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]([C:14]1[CH:15]=[C:16]([C:26]([CH3:30])([CH3:29])[C:27]#[N:28])[CH:17]=[C:18]([CH2:20][N:21]2[CH:25]=[N:24][CH:23]=[N:22]2)[CH:19]=1)[CH3:13].C(N(CC)CC)C>ClCCl.O>[C:12]([C:14]1[CH:15]=[C:16]([C:26]([CH3:30])([CH3:29])[C:27]#[N:28])[CH:17]=[C:18]([CH2:20][N:21]2[CH:25]=[N:24][CH:23]=[N:22]2)[CH:19]=1)(=[O:11])[CH3:13]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 19349402HCID 19349402, compound

Product 1

HCID 54249399HCID 54249399, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of oxalyl chloride (0.12 ml) in dichloromethane (2 ml) was stirred and cooled to 70° while dimethyl sulphoxide (0.12 ml) was added dropwise. The solution was stirred for 2 minutes, then 2-[3-(1-hydroxyethyl)-5-(1H-1,2,4-triazol-1-ylmethyl)phenyl]-2-methylpropiononitrile, (0.18 g), was added, and the temperature was kept at -70° for 10 minutes. Triethylamine (0.2 ml) was added, and the mixture was allowed to warm to room temperature. Water (15 ml) was added, and the mixture was extracted three times with dichloromethane. The extracts were combined, dried and evaporated to dryness, and the residue was purified by flash column chromatography, eluting with methanol:chloroform (1:99 by volume) to give 2-[3 acetyl-5-(1H-1,2,4-triazol-1 ylmethyl)phenyl]-2-methylpropiononitrile. Nmr in deuteriochloroform; δ 8.2(1H,s), 8.02(2H,m), 7.8(1H,m), 7.64(1H,m), 5.45(2H,s), 2.6 (3H,s), 1.75(6H,s).

Workup

  1. additionwas added dropwise
  2. waitthe temperature was kept at -70° for 10 minutes
  3. extractionthe mixture was extracted three times with dichloromethane
  4. customdried
  5. customevaporated to dryness
  6. customthe residue was purified by flash column chromatography
  7. washeluting with methanol:chloroform (1:99 by volume)

Sources & evidence

ORD record
ord-ea4ab7f31ff84a55a66b2f3514d2b4d9
Source dataset
uspto-grants-1990_06
Patent number
US04935437

Reaction notes

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