m-Tolyl isocyanate → HCID 18940633, compound

HRID 1591248Notes

Reaction equation

HRID 1591248 reaction equation
[NH2:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[NH:4][C:3]1=[S:19].[C:20]1([CH3:29])[CH:25]=[CH:24][CH:23]=[C:22]([N:26]=[C:27]=[O:28])[CH:21]=1>O1CCCC1>[CH3:29][C:20]1[CH:21]=[C:22]([NH:26][C:27]([NH:1][CH:2]2[N:8]=[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:6]3[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=3[NH:4][C:3]2=[S:19])=[O:28])[CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 19766209HCID 19766209, compound

Product 1

HCID 18940633HCID 18940633, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1,3-Dihydro-3-amino-5-phenyl-2H-1,4-benzodiazepin-2-thione (400 mg, 1.5 mmole) and m-tolylisocyanate (194 μL, 1.5 mmole) were combined in 40 mL of dry tetrahydrofuran at 0° C. The reaction mixture was warmed to room temperature over a 1 hour period and diluted with 20 mL of tetrahydrofuran. The reaction mixture was filtered and concentrated under reduced pressure. The residual material was chromatographed on silica gel (96:4:0.4 chloroform-methanol-concentrated ammonium hydroxide) to give 480 mg of the title compound analytically pure after trituration with ether/petroleum ether:

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe residual material was chromatographed on silica gel (96:4:0.4 chloroform-methanol-concentrated ammonium hydroxide)

Sources & evidence

ORD record
ord-4f5b255e6d0b4627b5a0d0902539c694
Source dataset
uspto-grants-1993_04
Patent number
US05206237

Reaction notes

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