Triphosgene → HCID 86717347, compound

HRID 527145Notes

Reaction equation

HRID 527145 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].Cl[C:25](Cl)([O:27]C(=O)OC(Cl)(Cl)Cl)Cl.Cl.[CH3:37][O:38][NH2:39]>C1COCC1>[CH:19]([C:16]1[CH:17]=[CH:18][C:13]([C:2]2([NH:1][C:25]([NH:39][O:38][CH3:37])=[O:27])[C:10](=[O:11])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]2=[O:12])=[C:14]([O:22][CH3:23])[CH:15]=1)([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 94429TriphosgeneHCID 521874O-Methylhydroxylamine hydrochlorideHCID 86717345HCID 86717345, compound

Product 1

HCID 86717347HCID 86717347, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-amino-2-(4-isopropyl-2-methoxyphenyl)-2H-inden-1,3-dione (0.50 g, 1.61 mmol) in anhydrous THF (20 ml) was added triphosgene (0.528 g, 1.77 mmol) and stirred for 15 min. The reaction mixture was concentrated and was dissolved in anhydrous THF (20 ml) and was added O-methyl-hydroxylamine hydrochloride (0.28 g, 4.04 mmol) was stirred for 2 hrs at room temperature. The reaction mixture was oncentrated and was purified using silica gel column chromatography (1:1=ethylacetate:hexane) to afford the title compound (420 mg, 69%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionwas dissolved in anhydrous THF (20 ml)
  3. stirringwas stirred for 2 hrs at room temperature
  4. customwas purified

Sources & evidence

ORD record
ord-4dbcf232a8d64c98933cb24e46e1c68d
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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