2-(Trifluoromethyl)phenyl isothiocyanate → 4H-Pyrido(4',3':4,5)thieno(3,2-f)(1,2,4)triazolo(4,3-a)(1,4)diazepine-9(8H)-carbothioamide, 7,10-dihydro-6-(2-chlorophenyl)-1-methyl-N-(2-(trifluoromethyl)phenyl)-

HRID 1744207Notes

Reaction equation

HRID 1744207 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]=[C:10]=[S:11].[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[C:27]2[C:28]3[CH2:34][CH2:33][NH:32][CH2:31][C:29]=3[S:30][C:26]=2[N:25]2[C:35]([CH3:38])=[N:36][N:37]=[C:24]2[CH2:23][N:22]=1>ClCCCl>[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[C:27]2[C:28]3[CH2:34][CH2:33][N:32]([C:10](=[S:11])[NH:9][C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[C:2]([F:12])([F:1])[F:13])[CH2:31][C:29]=3[S:30][C:26]=2[N:25]2[C:35]([CH3:38])=[N:36][N:37]=[C:24]2[CH2:23][N:22]=1

Participants

4

Reactant 2

HCID 7371622-(Trifluoromethyl)phenyl isothiocyanateHCID 14071251HCID 14071251, compound

Product 1

HCID 30767784H-Pyrido(4',3':4,5)thieno(3,2-f)(1,2,4)triazolo(4,3-a)(1,4)diazepine-9(8H)-carbothioamide, 7,10-dihydro-6-(2-chlorophenyl)-1-methyl-N-(2-(trifluoromethyl)phenyl)-

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture containing 2-trifluoromethylphenyl isothiocyanate (0.82 g, 0.004 mol) and 6-(2-chlorophenyl)-7,8,9,10-tetrahydro-1-methyl-4H-pyrido[4′,3′;4,5]thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine (1 g, 0.0027 mol) in 30 ml of 1,2-dichloroethane is agitated for 4 hours and at a temperature close to 20° C. Half the solvent is evaporated off with the rotary evaporator then 10 ml of ether is added. Agitation is carried out for 20 minutes at a temperature close to 20° C. followed by filtering on frit then washing with 20 ml of ether, with 20 ml of isopropyl ether and with 20 ml of isopentane. After drying under vacuum a cream coloured solid is obtained (1.21 g, 78%). Melting point: 190–192° C.

Workup

  1. customclose to 20° C
  2. customHalf the solvent is evaporated off with the rotary evaporator
  3. addition10 ml of ether is added
  4. waitAgitation is carried out for 20 minutes at a temperature
  5. customclose to 20° C.
  6. filtrationby filtering on frit
  7. washthen washing with 20 ml of ether, with 20 ml of isopropyl ether and with 20 ml of isopentane
  8. customAfter drying under vacuum a cream
  9. customis obtained (1.21 g, 78%)

Sources & evidence

ORD record
ord-96f9d64d23b3477096b29c3d955a520b
Source dataset
uspto-grants-2006_03
Patent number
US07015213B1

Reaction notes

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