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

HRID 1768637Notes

Reaction equation

HRID 1768637 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 ml 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 (CDCl3): δ (ppm)=2.5 (m,2H), 2.92 (t,2H), 6.54 (t,2H), 7.2 (d,lH), 7.29 (d,1H), 7.5 (dd,1H), 7.55 (d,1H), 8.5 (d,1H).

Sources & evidence

ORD record
ord-5b6b09f15bba4bfea3ebb17617bb633a
Source dataset
uspto-grants-1995_01
Patent number
US05378721

Reaction notes

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