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

HRID 1939220
Notes
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Reaction equation

HRID 1939220 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 691942-Tolyl isocyanateHCID 214671424-(4-Aminobenzoyl)-5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine

Product 1

HCID 190290505,6,7,8-Tetrahydro-4-[4-[[[(2-methylphenyl)amino]carbonyl]amino]benzoyl]-4H-thieno[3,2-b]azepineYield 54.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

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

Sources & evidence

ORD record
ord-d33aa7c40fee47ab921f925c68d2f175
Source dataset
uspto-grants-1997_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05696112

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes