4-Nitrobenzoyl isothiocyanate → N-((7-bromo-3-chloro-5-(2-hydroxyethyl)-5H-chromeno[2,3-c]pyridin-5-yl)carbamothioyl)-4-nitrobenzamide

HRID 931601Notes

Reaction equation

HRID 931601 reaction equation
[NH2:1][C:2]1([CH2:18][CH2:19][OH:20])[C:15]2[CH:14]=[C:13]([Cl:16])[N:12]=[CH:11][C:10]=2[O:9][C:8]2[C:3]1=[CH:4][C:5]([Br:17])=[CH:6][CH:7]=2.[N+:21]([C:24]1[CH:34]=[CH:33][C:27]([C:28]([N:30]=[C:31]=[S:32])=[O:29])=[CH:26][CH:25]=1)([O-:23])=[O:22]>C1COCC1>[Br:17][C:5]1[CH:4]=[C:3]2[C:8](=[CH:7][CH:6]=1)[O:9][C:10]1[CH:11]=[N:12][C:13]([Cl:16])=[CH:14][C:15]=1[C:2]2([NH:1][C:31]([NH:30][C:28](=[O:29])[C:27]1[CH:26]=[CH:25][C:24]([N+:21]([O-:23])=[O:22])=[CH:34][CH:33]=1)=[S:32])[CH2:18][CH2:19][OH:20]

Participants

4

Reactant 2

HCID 1413984-Nitrobenzoyl isothiocyanateHCID 77230928HCID 77230928, compound

Product 1

HCID 86658374N-((7-bromo-3-chloro-5-(2-hydroxyethyl)-5H-chromeno[2,3-c]pyridin-5-yl)carbamothioyl)-4-nitrobenzamideYield 112.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A reaction mixture of 2-(5-amino-7-bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-yl)ethanol (2.8 g, 7.87 mmol) and 4-nitrobenzoyl isothiocyanate (1.639 g, 7.87 mmol) in THF (100 mL) was stirred at RT for 1 hour. The reaction mixture was then concentrated under reduced pressure to afford N-(7-bromo-3-chloro-5-(2-hydroxyethyl)-5H-chromeno[2,3-c]pyridin-5-ylcarbamothioyl)-4-nitrobenzamide (5 g, 8.87 mmol).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-1e0662b7ce774e4a85493b0fe3ba85e0
Source dataset
uspto-grants-2016_03
Patent number
US09296759B2

Reaction notes

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