2-Mercaptoethanol → HCID 178509464, compound

HRID 1095452Notes

Reaction equation

HRID 1095452 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.O[C:13]1([C:25]2[NH:26][CH:27]=[N:28][CH:29]=2)[CH2:22][CH2:21][CH2:20][C:19]2[CH:18]=[C:17]([C:23]#[N:24])[CH:16]=[CH:15][C:14]1=2.[SH:30][CH2:31][CH2:32][OH:33]>C1(C)C(C)=CC=CC=1.C(=O)(O)[O-].[Na+]>[OH:33][CH2:32][CH2:31][S:30][C:18]1[C:19]2[CH2:20][CH2:21][CH2:22][CH:13]([C:25]3[N:26]=[CH:27][NH:28][CH:29]=3)[C:14]=2[CH:15]=[CH:16][C:17]=1[C:23]#[N:24]

Participants

6

Reactant 3

HCID 15672-MercaptoethanolHCID 6101p-Toluenesulfonic acidHCID 667822465-hydroxy-5-(3H-imidazol-4-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Product 1

HCID 178509464HCID 178509464, compound

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

5 mol % p-toluenesulphonic acid are added to a solution of 1 mmol of 5-hydroxy-5-(3H-imidazol-4-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile and 2.2 mmol of 2-mercaptoethanol [60-24-2] in 10 ml of xylene, and the mixture is heated to reflux in the presence of molecular sieves (4 Å) overnight. The reaction mixture is cooled to room temperature, diluted with 1M sodium bicarbonate solution and extracted with ethyl acetate (3×). The combined organic phases are dried with sodium sulphate and evaporated. The title compound is identified from the residue on the basis of the Rf by flash chromatography (SiO2 60F).

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux in the presence of molecular sieves (4 Å) overnight
  3. extractionextracted with ethyl acetate (3×)
  4. dry with materialThe combined organic phases are dried with sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-e54bce79ec2e4a47a9442ec23acbe555
Source dataset
uspto-grants-2012_03
Patent number
US08138179B2

Reaction notes

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