Acetyl chloride → HCID 22158986, compound

HRID 1089385Notes

Reaction equation

HRID 1089385 reaction equation
[NH2:1][CH2:2][CH2:3][S:4][Sn:5]([CH2:14][CH2:15][CH2:16][CH3:17])([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9].C(N(CC)CC)C.[C:25](Cl)(=[O:27])[CH3:26]>C1COCC1>[C:25]([NH:1][CH2:2][CH2:3][S:4][Sn:5]([CH2:6][CH2:7][CH2:8][CH3:9])([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:10][CH2:11][CH2:12][CH3:13])(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 127188782-[(Tributylstannyl)sulfanyl]ethan-1-amine

Product 1

HCID 22158986HCID 22158986, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(2-Aminoethylthio)tri-n-butyltin (6.8 mmol, 2.5 g) and triethylamine (6.8 mmol, 687 mg) were dissolved in THF (75 ml). This mixture was cooled to 0° C. and acetyl chloride was added dropwise, and the resultant mixture stirred at 22° C. for 16 h. The solvent was evaporated, the residue was suspended in ether (50 ml), and the precipitated triethylamine hydrochloride was removed by filtration. The salt was washed with ether (20 ml), and the combined organic phases were washed with water (25 ml), dried and evaporated to leave the crude product which was purified by column chromatography leaving the pure amide (13) as a colourless oil (2.35 g, 85%). All spectroscopic and analytical data were consistent with the proposed structure.

Workup

  1. customThe solvent was evaporated
  2. customthe precipitated triethylamine hydrochloride was removed by filtration
  3. washThe salt was washed with ether (20 ml)
  4. washthe combined organic phases were washed with water (25 ml)
  5. customdried
  6. customevaporated
  7. customto leave the crude product which
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-d6fa4f63c4a143b399df9cda06412071
Source dataset
uspto-grants-1990_10
Patent number
US04966678

Reaction notes

Loading…