Methyl iodide → 3,4-dihydro-5-methyl-2H-1,5-benzothiazepine

HRID 1463405Notes

Reaction equation

HRID 1463405 reaction equation
Br.[S:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][CH2:5][CH2:4][CH2:3]1.[Li][CH2:14]CCC.CI>C1COCC1>[CH3:14][N:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[S:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 19935412HCID 19935412, compoundHCID 178418339Butyllithium

Product 1

HCID 199354143,4-dihydro-5-methyl-2H-1,5-benzothiazepine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8.30 g of 3,4-dihydro-2H-1,5-benzothiazepine hydrobromide were placed in 150 ml of THF and deprotonized with 48 ml of 1.55M nBuLi (hexane) under an Argon atmosphere at -10° C. After 1/4 hour, 4.64 ml of Methyl iodide (MeI) were added dropwise to the yellow solution of the Li amide and the mixture was stirred for 1 hour. It was then poured on to ice, extracted with ether, washed with water, dried and evaporated. Column chromatography on silica gel (petroleum ether/ethyl acetate 96/4) yielded 5.70 g of 3,4-dihydro-5-methyl-2H-1,5-benzothiazepine as a colorless oil which was formulated as follows:

Workup

  1. waitAfter 1/4 hour
  2. additionIt was then poured on to ice
  3. extractionextracted with ether
  4. washwashed with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-62b86f07f6894536abfee804971c3f77
Source dataset
uspto-grants-1994_04
Patent number
US05300522

Reaction notes

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