Thiophosgene → N-[3-[(7,8-Didehydro-4,5-epoxy-6-hydroxy-17-methylmorphinan-3-yl)oxy]propoxy]-4-isothiocyanatobenzamide

HRID 53296Notes

Reaction equation

HRID 53296 reaction equation
[O:1]1[CH:13]2[C@@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@@H:9]3[CH:10]=[CH:11][CH:12]2[OH:20])[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3]([O:21][CH2:22][CH2:23][CH2:24][O:25][NH:26][C:27](=[O:35])[C:28]1[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=1)[CH:4]=[CH:5]2.C(=O)(O)[O-].[Na+].[C:41](Cl)(Cl)=[S:42]>C(Cl)Cl>[O:1]1[CH:13]2[C@@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@@H:9]3[CH:10]=[CH:11][CH:12]2[OH:20])[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3]([O:21][CH2:22][CH2:23][CH2:24][O:25][NH:26][C:27](=[O:35])[C:28]1[CH:29]=[CH:30][C:31]([N:34]=[C:41]=[S:42])=[CH:32][CH:33]=1)[CH:4]=[CH:5]2

Participants

5

Reactant 3

HCID 10040ThiophosgeneHCID 516892Sodium BicarbonateHCID 86750690N-[3-[(7,8-Didehydro-4,5-epoxy-6-hydroxy-17-methylmorphinan-3-yl)oxy]propoxy]-4-aminobenzamide

Product 1

HCID 86750689N-[3-[(7,8-Didehydro-4,5-epoxy-6-hydroxy-17-methylmorphinan-3-yl)oxy]propoxy]-4-isothiocyanatobenzamideYield 40.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 0.5 g (1.1 mmol) of N-[3-[(7,8-Didehydro-4,5-epoxy-6-hydroxy-17-methylmorphinan-3-yl)oxy]propoxy]-4-aminobenzamide in 10 ml of methylene chloride was treated with 0.5 g of solid anhydrous sodium bicarbonate followed by 150 ul (1.9 mmol) of thiophosgene and stirred at room temperature for 30 minutes. The solvent was removed in vacuo and the residue was chromatographed on 150 g of silica gel using 15% methanol-chloroform to give 230 mg of N-[3-[(7,8-Didehydro-4,5-epoxy-6-hydroxy-17-methylmorphinan-3-yl)oxy]propoxy]-4-isothiocyanatobenzamide as an amorphous solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was chromatographed on 150 g of silica gel using 15% methanol-chloroform

Sources & evidence

ORD record
ord-3350fdc4317644f1a3832cb291f379e6
Source dataset
uspto-grants-1997_04
Patent number
US05618926

Reaction notes

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