Thiophenol → HCID 23462870, compound

HRID 2286393Notes

Reaction equation

HRID 2286393 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:11]1[C:21]2[CH2:20][CH2:19][N:18]([CH3:22])[CH2:17][CH2:16][C:15]=2[C:14]([N+:23]([O-:25])=[O:24])=[CH:13][CH:12]=1>CN(C)C=O>[CH3:22][N:18]1[CH2:17][CH2:16][C:15]2[C:14]([N+:23]([O-:25])=[O:24])=[CH:13][CH:12]=[C:11]([S:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:21]=2[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 24758Sodium hydrideHCID 13338331HCID 13338331, compound

Product 1

HCID 23462870HCID 23462870, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
25 °C

Procedure

To a stirred solution of 11.0 g. (0.1 mole) of thiophenol in 200 ml. of dimethylformamide at 0°-10° C., under an atmosphere of nitrogen, is added cautiously, in portions, 4.65 g. (0.11 mole) of a 57% dispersion of sodium hydride in mineral oil. The resulting solution is stirred for 15 minutes at 25° C. and then a solution of 24.1 g. (0.1 mole) of 6-chloro-3-methyl-9-nitro-2,3,4,5-tetrahydro-1H-3-benzazepine in 50 ml. of dimethylformamide is added dropwise. The reaction mixture is heated at 100° C. for 2 hours, then it is cooled to 25° C. and poured into ice/water. The resulting solid is filtered, air-dried and recrystallized from ethyl acetate-hexane to give 3-methyl-9-nitro-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine.

Workup

  1. temperatureThe reaction mixture is heated at 100° C. for 2 hours
  2. temperatureit is cooled to 25° C.
  3. filtrationThe resulting solid is filtered
  4. customair-dried
  5. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-dc8d77c8a9ed4828a891a6a9acba38b7
Source dataset
uspto-grants-1981_05
Patent number
US04265890

Reaction notes

Loading…