Triethylamine → 4-Acryloyl-2,3,4,5-tetrahydro-1,4-benzothiazepine

HRID 36562Notes

Reaction equation

HRID 36562 reaction equation
[S:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:19](Cl)(=[O:22])[CH:20]=[CH2:21].[OH-].[K+]>C1COCC1>[C:19]([N:4]1[CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[S:1][CH2:2][CH2:3]1)(=[O:22])[CH:20]=[CH2:21]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 14797Potassium HydroxideHCID 122691062,3,4,5-Tetrahydrobenzo[f][1,4]thiazepine

Product 1

HCID 152916564-Acryloyl-2,3,4,5-tetrahydro-1,4-benzothiazepine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,3,4,5-Tetrahydro-1,4-benzothiazepine (11 g) and triethylamine (13.5 g) were dissolved in THF (300 ml) and acryloyl chloride (9.5 g) was added dropwise thereto under ice cooling and agitated at room temperature for 30 minutes. A 10% potassium hydroxide aqueous solution was added thereto, agitated at room temperature and thereafter extracted with chloroform. The chloroform phase was washed with a saturated saline solution and dried on sodium sulfate and the solvent was distilled out under reduced pressure. Residue was purified by silica gel column chromatography (Wako Gel C-200, 200 g) and eluted with a mixed solvent of n-hexane (60 parts) +ethyl acetate (40 parts) to give 4-acryloyl-2,3,4,5-tetrahydro-1,4-benzothiazepine (12.59).

Workup

  1. stirringagitated at room temperature
  2. extractionextracted with chloroform
  3. washThe chloroform phase was washed with a saturated saline solution
  4. customdried on sodium sulfate
  5. distillationthe solvent was distilled out under reduced pressure
  6. customResidue was purified by silica gel column chromatography (Wako Gel C-200, 200 g)
  7. washeluted with a mixed solvent of n-hexane (60 parts) +ethyl acetate (40 parts)

Sources & evidence

ORD record
ord-f3e2f312ed3c480da71fc70278c3f2e3
Source dataset
uspto-grants-1995_05
Patent number
US05416066

Reaction notes

Loading…