Pyridine → HCID 54491580, compound

HRID 648769

Reaction equation

HRID 648769 reaction equation
N1C=CC=CC=1.[OH:7][N:8]=[C:9]([C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)[C:10]#[N:11].[C:17]([O:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1)(=[O:19])[CH3:18].C(OCC)C>CN(C)C1C=CN=CC=1.O1CCCC1>[C:17]([O:20][C:21]1[CH:22]=[CH:23][C:24]([S:27]([O:7][N:8]=[C:9]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)[C:10]#[N:11])(=[O:29])=[O:28])=[CH:25][CH:26]=1)(=[O:19])[CH3:18]

Participants

7

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 129257104-(Chlorosulfonyl)phenyl acetateHCID 73667355Alpha-Oximino-2-Thienylacetonitrile

Product 1

HCID 54491580HCID 54491580, compoundYield 53.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

200 mg of 4-dimethylaminopyridine and 6.2 g (0.08 mole) of pyridine are added to a solution of 12 g (0.08 mole) of α-hydroxyiminothien-2-ylacetonitrile (3b) in 75 ml of tetrahydrofuran. With cooling to 0° C., a solution of 18.5 g (0.08 mole) of 4-acetoxybenzenesulfonyl chloride (3a) in 30 ml of tetrahydrofuran is added dropwise. The reaction mixture is stirred for 16 hours at room temperature, and 100 ml of diethyl ether are subsequently added. The precipitated salts are removed by filtration and the solution is concentrated by evaporation. The residual crude product is recrystallised from hexane/ethyl acetate, affording 15 g of crystals with a melting point of 114°-115° C.

Workup

  1. customThe precipitated salts are removed by filtration
  2. concentrationthe solution is concentrated by evaporation
  3. customThe residual crude product is recrystallised from hexane/ethyl acetate

Sources & evidence

ORD record
ord-6e35bdfa6f57408fb75bc914e9662299
Source dataset
uspto-grants-1988_04
Patent number
US04736055

Linked notes

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