(+-)-Methionine → 8-hydroxy-7-methoxy-3-methyl-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 2286404Notes

Reaction equation

HRID 2286404 reaction equation
C(O)(=O)/C=C/C(O)=O.[CH3:9][O:10][C:11]1[C:22]([O:23]C)=[CH:21][C:14]2[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19][C:13]=2[C:12]=1[S:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.NC(C(O)=O)CCSC.CS(O)(=O)=O>>[OH:23][C:22]1[C:11]([O:10][CH3:9])=[C:12]([S:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:13]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15][C:14]=2[CH:21]=1

Participants

4

Reactant 3

HCID 876(+-)-MethionineHCID 6395Methanesulfonic AcidHCID 23462871HCID 23462871, compound

Product 1

HCID 234628598-hydroxy-7-methoxy-3-methyl-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepineYield 87%

Procedure

A mixture of 2.6 g. (0.008 mole) of 7,8-dimethoxy-3-methyl-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine (prepared as in Example 3) and 1.26 g. (0.0085 mole) of dl-methionine in 35 ml. of methanesulfonic acid was stirred at room temperature for 3.5 hours. The reaction mixture was quenched with ice/water, made basic with 10% sodium hydroxide solution to pH 8.5 and extracted with chloroform. The extract was washed with saturated sodium chloride solution, dried over sodium sulfate and evaporated to give 2.18 g. (87% yield) of 8-hydroxy-7-methoxy-3-methyl-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine, m.p. 161°-162° C.

Workup

  1. additionA mixture of 2.6 g
  2. customThe reaction mixture was quenched with ice/water
  3. extractionextracted with chloroform
  4. washThe extract was washed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customto give 2.18 g

Sources & evidence

ORD record
ord-e1e3373c103c4984ab993dedb0a087d6
Source dataset
uspto-grants-1981_05
Patent number
US04265890

Reaction notes

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