2-Tolyl isocyanate → 5,6,7,8-Tetrahydro-4-[4-[[[(2-methylphenyl)amino]carbonyl]amino]benzoyl]-4H-thieno[3,2-b]azepine

HRID 2255991Notes

Reaction equation

[NH2:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([N:8]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]3[S:15][CH:16]=[CH:17][C:9]2=3)=[O:7])=[CH:4][CH:3]=1.[CH3:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N:27]=[C:28]=[O:29]>O1CCCC1>[CH3:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[NH:27][C:28]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]3[S:15][CH:16]=[CH:17][C:9]2=3)=[O:7])=[CH:18][CH:19]=1)=[O:29]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 0.409 g of 4-(4-aminobenzoyl)-5,6,7,8-tetrahydro-4H-thieno [3,2-b]azepine and 0.60 g of 2-methylphenylisocyanate in 2 ml of tetrahydrofuran is heated in an oil bath at 110° C. for 16 hours. The mixture is concentrated under vacuum and the residue chromatographed on preparative silica gel plates with ethyl acetate-hexane (1:1) as solvent to give a solid. Crystallization from ethyl acetate-hexane gives 0.33 g of white crystals, m.p. 179°-182° C.

Workup

concentrationThe mixture is concentrated under vacuum
customthe residue chromatographed on preparative silica gel plates with ethyl acetate-hexane (1:1) as solvent
customto give a solid
customCrystallization from ethyl acetate-hexane

Sources & evidence

ORD record: ord-3837ce5e65e544789cf320b2e09491eb
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05654297

Reaction notes

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