Toluene → HCID 23462925, compound

HRID 2286414Notes

Reaction equation

HRID 2286414 reaction equation
Br[C:2]1[C:7]2[CH2:8][CH2:9][N:10]([CH3:13])[CH2:11][CH2:12][C:6]=2[C:5]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:4]([O:21][CH3:22])[C:3]=1[O:23][CH3:24].C1(C)C=CC=CC=1.C([Li])CCC.[OH-].[Na+].CN(C)[CH:41]=[O:42]>CCCCCC>[CH3:22][O:21][C:4]1[C:3]([O:23][CH3:24])=[C:2]([CH:41]=[O:42])[C:7]2[CH2:8][CH2:9][N:10]([CH3:13])[CH2:11][CH2:12][C:6]=2[C:5]=1[S:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 5

HCID 1140TolueneHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 23462866HCID 23462866, compoundHCID 178418339Butyllithium

Product 1

HCID 23462925HCID 23462925, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a solution of 18.21 g. (0.0446 mole) of 9-bromo-7,8-dimethoxy-3-methyl-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine (prepared as in Example 20) in 200 ml. of toluene, cooled to -78° C., is slowly added 26.0 ml. of 2.1 M n-butyl lithium in hexane. After 20 minutes at this temperature 23.1 ml. of dimethylformamide is added and the mixture is stirred for 1/2 hour. The reaction mixture, at room temperature, is poured into 10% sodium hydroxide solution and extracted with ethyl acetate. The extract is washed with water, dried and concentrated to give 7,8-dimethoxy-3-methyl-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine-9-carboxaldehyde.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8a509ee9c21344a192df5de3d5ed06e5
Source dataset
uspto-grants-1981_05
Patent number
US04265890

Reaction notes

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