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

HRID 373562Notes

Reaction equation

HRID 373562 reaction equation
Br.[N:2]1[CH2:3]C[S:5][CH:6]=[C:7]2C=CC=C[C:8]=12.[Li][CH2:14][CH2:15][CH2:16][CH3:17].CI.[CH2:20]1COC[CH2:21]1>>[CH3:3][N:2]1[C:16]2[CH:15]=[CH:14][CH:20]=[CH:21][C:17]=2[S:5][CH2:6][CH2:7][CH2:8]1

Participants

5

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 19810499HCID 19810499, compoundHCID 178418339Butyllithium

Product 1

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

Procedure

8.30 g of 3,4-dihydro-2H-2,5-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 formylated 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-e6513137f84e46709bd5a30b479fbf93
Source dataset
uspto-grants-1992_11
Patent number
US05164387

Reaction notes

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