4-Isothiocyanato-2-(trifluoromethyl)benzonitrile → 4-(8-Imino-6-thioxo-5-(4-methylphenyl)-5,7-diazaspiro[3.4]oct-7-yl)-2-trifluoromethylbenzonitrile

HRID 244977Notes

Reaction equation

HRID 244977 reaction equation
[N:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([C:12]([F:15])([F:14])[F:13])[CH:5]=1)=[C:2]=[S:3].[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]2([C:28]#[N:29])[CH2:27][CH2:26][CH2:25]2)=[CH:19][CH:18]=1>CN(C=O)C>[NH:29]=[C:28]1[C:24]2([CH2:27][CH2:26][CH2:25]2)[N:23]([C:20]2[CH:19]=[CH:18][C:17]([CH3:16])=[CH:22][CH:21]=2)[C:2](=[S:3])[N:1]1[C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([C:12]([F:13])([F:15])[F:14])[CH:5]=1

Participants

4

Reactant 2

HCID 116155404-Isothiocyanato-2-(trifluoromethyl)benzonitrileHCID 609877761-(4-Methylphenyl)aminocyclobutanenitrile

Product 1

HCID 159527814-(8-Imino-6-thioxo-5-(4-methylphenyl)-5,7-diazaspiro[3.4]oct-7-yl)-2-trifluoromethylbenzonitrileYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1a (2.28 g, 10 mmol) in dry DMF (3 ml) was added progressively, over 20 hours, a solution of 7a (1.764 g, 9 mmol) in dry DMF (3 ml) at room temperature. The medium was stirred for an additional 4 h. After DMF being evaporated, the residue was chromatographed (dichloromethane/acetone, 95:5) to afford 4-(8-imino-6-thioxo-5-(4-methylphenyl)-5,7-diazaspiro[3.4]oct-7-yl)-2-trifluoromethylbenzonitrile, 7b (1.937 g, 4.68 mmol, 52%).

Workup

  1. customat room temperature
  2. customAfter DMF being evaporated
  3. customthe residue was chromatographed (dichloromethane/acetone, 95:5)

Sources & evidence

ORD record
ord-5a04ca0dccab4085b3ab7dcd5d8f4c0d
Source dataset
uspto-grants-2014_02
Patent number
US08658681B2

Reaction notes

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