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Ethylamine → HCID 71477444, compound

HRID 527144
Notes
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Reaction equation

HRID 527144 reaction equation
[NH2:1][C:2]1([C:13]2[CH:18]=[CH:17][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:15][C:14]=2[O:22][CH3:23])[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12].ClC(Cl)(O[C:28](=[O:34])OC(Cl)(Cl)Cl)Cl.[CH2:36]([NH2:38])[CH3:37].ClCCl>C1COCC1>[CH2:36]([NH:38][C:28]([NH:1][C:2]1([C:13]2[CH:18]=[CH:17][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:15][C:14]=2[O:22][CH3:23])[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12])=[O:34])[CH3:37]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6341EthylamineHCID 6344DichloromethaneHCID 94429TriphosgeneHCID 86717345HCID 86717345, compound

Product 1

HCID 71477444HCID 71477444, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

A solution of 2-amino-2-(4-isopropyl-2-methoxyphenyl)-2H-inden-1,3-dione (0.50 g, 1.62 mmol) in anhydrous THF (10 ml) was added triphosgene (0.52 g, 1.77 mmol) and stirred for 15 min. The reaction mixture was concentrated and was dissolved in anhydrous THF (10 ml) and was added ethylamine (2.0M in methanol, 2 mL, 400 mmol) and was stirred for 2 hrs. Concentrated reaction mixture was added dichloromethane to afford the title compound (450 mg, 74%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionwas dissolved in anhydrous THF (10 ml)
  3. stirringwas stirred for 2 hrs
  4. concentrationConcentrated
  5. customreaction mixture

Sources & evidence

ORD record
ord-af9f2ed056dc4a4fa34e04360827f707
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09346749B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes