Acetic Anhydride → 1-(2,3-Dihydro-1,4-benzothiazepin-4(5H)-yl)ethanone

HRID 1910437Notes

Reaction equation

HRID 1910437 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](OC(=O)C)(=[O:21])[CH3:20]>ClCCl>[S:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][N:4]([C:19](=[O:21])[CH3:20])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 122691062,3,4,5-Tetrahydrobenzo[f][1,4]thiazepine

Product 1

HCID 146707161-(2,3-Dihydro-1,4-benzothiazepin-4(5H)-yl)ethanoneYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,3,4,5-tetrahydro-1,4-benzothiazepine (5 g, 30.3 mmol) in dry dichloromethane (100 mL) was added triethylamine (5.06 mL, 36.3 mmol) at room temperature, followed by the addition of acetic anhydride (3.43 mL, 36.3 mmol) dropwise at 0° C. under nitrogen. The resulting solution was stirred for 1 hour whilst allowing the temperature to rise slowly to room temperature. The mixture was washed with brine (50 mL×2), dried over sodium sulfate, filtered and concentrated in vacuo to afford 6.28 g of product as yellow oil, which was used for next step without further purification.

Workup

  1. customto rise slowly to room temperature
  2. washThe mixture was washed with brine (50 mL×2)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-385c5c827fcd4431925ff99cac654ca1
Source dataset
uspto-grants-2013_12
Patent number
US08604019B2

Reaction notes

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