4-Chlorophenyl Isocyanate → HCID 18940641, compound

HRID 1591247Notes

Reaction equation

HRID 1591247 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].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][CH:22]=1>O1CCCC1>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([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:29])=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 19766209HCID 19766209, compound

Product 1

HCID 18940641HCID 18940641, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1,3-Dihydro-3-amino-5-phenyl-2H-1,4-benzodiazepin-2-thione (1.5 mmole) and 4-chlorophenylisocyanate (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 the title compound analytically pure after trituration with ether/petroleum ether: the 1HNMR spectrum is consistent with the structure of the title compound.

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-c38123a9a676475f94830062275c2012
Source dataset
uspto-grants-1993_04
Patent number
US05206237

Reaction notes

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