Hydrochloric Acid → HCID 21242957, compound

HRID 542740Notes

Reaction equation

HRID 542740 reaction equation
Br[C:2]1[C:12]2[CH2:11][CH2:10][N:9]([CH3:13])[CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([O:14][CH3:15])[CH:3]=1.C([Li])CCC.[CH3:21][S:22]SC.Cl>C1(C)C=CC=CC=1.O>[CH3:15][O:14][C:4]1[CH:3]=[C:2]([S:22][CH3:21])[C:12]2[CH2:11][CH2:10][N:9]([CH3:13])[CH2:8][CH2:7][C:6]=2[CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12232Dimethyl DisulfideHCID 21242899HCID 21242899, compoundHCID 178418339Butyllithium

Product 1

HCID 21242957HCID 21242957, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent3×

Procedure

A solution of 6-bromo-8-methoxy-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (2.7 g, 0.01 m) in toluene (30 ml) is added to a solution of n-butyl lithium (0.044 m) in toluene (15 ml) stirred at -78°. The mixture is stirred for thirty minutes, treated with a solution of methyl disulfide (8.2 g, 0.087 m) in toluene (10 ml), stirred for fifteen minutes and poured into water (125 ml). The mixture is acidified with 10% hydrochloric acid and the aqueous phase is washed with ether, made alkaline with aqueous sodium hydroxide and extracted with ethyl acetate. The ethyl acetate extract is washed, dried with sodium sulfate and concentrated in vacuo to give 8-methoxy-3-methyl-6-methylthio-2,3,4,5-tetrahydro-1H-3-benzazepine.

Workup

  1. stirringThe mixture is stirred for thirty minutes
  2. stirringstirred for fifteen minutes
  3. washthe aqueous phase is washed with ether
  4. extractionextracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. washis washed
  7. dry with materialdried with sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e7e45f2102c74415b68481c60da34c41
Source dataset
uspto-grants-1987_04
Patent number
US04659706

Reaction notes

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