Morpholine → 6-Cyano-1-(5-isothiazolyl)-3,4-dihydronaphthalene

HRID 5936Notes

Reaction equation

HRID 5936 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](O)([C:13]1[S:17][N:16]=[CH:15][CH:14]=1)[CH2:8][CH2:7][CH2:6]2)#[N:2].S(Cl)(Cl)=O.N1CCOCC1>C1C=CC=CC=1>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]1[S:17][N:16]=[CH:15][CH:14]=1)=[CH:8][CH2:7][CH2:6]2)#[N:2]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 24386Thionyl ChlorideHCID 189490166-Cyano-1-hydroxy-1-(5-isothiazolyl)-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 233653536-Cyano-1-(5-isothiazolyl)-3,4-dihydronaphthalene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Analogously to Example 13, 92 mg of 6-cyano-1-hydroxy-1-(5-isothiazolyl)-1,2,3,4-tetrahydronaphthalene (Example 15) and 0.051 ml of thionyl chloride in 0.32 of benzene, with the subsequent addition of 0.112 ml of morpholine, are converted into the crude title compound, which is purified by column chromatography (SiO2, 0.1 bar, hexane/ethyl acetate 4:1) and crystallisation from hexane; m.p. 77°-81°; 1H-NMR (CECl3): δ(ppm)=2.5 (m,2H), 2.92 (t,2H), 6.54 (t,2H), 7.2 (d,1H), 7.29 (d,1H), 7.5 (dd,1H), 7.55 (d,1H), 8.5 (d,1H).

Sources & evidence

ORD record
ord-9d47938a1fd34975a35c304222ad9c98
Source dataset
uspto-grants-1993_09
Patent number
US05246952

Reaction notes

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