Acetyl chloride → HCID 21963471, compound

HRID 2211878Notes

Reaction equation

HRID 2211878 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3N)[CH2:12][CH2:11]2)=[N:2]1.[CH2:25]([N:27](CC)CC)[CH3:26].C(Cl)(=[O:34])C>C(Cl)Cl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:19]=[CH:20][C:21]([NH:27][C:25](=[O:34])[CH3:26])=[CH:22][CH:23]=3)[CH2:12][CH2:11]2)=[N:2]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 21963169HCID 21963169, compound

Product 1

HCID 21963471HCID 21963471, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A round bottomed flask was charged with 0.528 g (1.5 mmol) (0.2-[2-(4-1,2-benzisothiazol-3-yl-piperazin-1-yl)-ethyl]-phenylamine, 6.2 mL CH2Cl2, 0.26 mL (1.8 mmol) triethylamine, and 0.15 mL (2 mmol) acetyl chloride. After 17 h at rt, the reaction was quenched with 1M NaHCO3. The organic layer was separated, dried, and concentrated in vacuo to give a white foam. This white foam was triturated with ether to give 0.36 g (61% yield) of the desired material as a white solid. MS (APCI): 381 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 7.89 (d, J=8 Hz, 1H), 7.9 (d, J=8 Hz, 1H), 7.47–7.24 (m, 4H), 7.18–7.14 (m, 3H), 3.59–3.56 (m, 4H), 2.84–2.63 (m, 8H), 2.15 (s, 3H).

Workup

  1. additionA round bottomed flask was charged with 0.528 g (1.5 mmol) (0
  2. customthe reaction was quenched with 1M NaHCO3
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customto give a white foam
  7. customThis white foam was triturated with ether

Sources & evidence

ORD record
ord-e9aa6f305705444c9cd054a1ae2015c9
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Reaction notes

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