Acetyl chloride → HCID 137329926, compound

HRID 2428110Notes

Reaction equation

HRID 2428110 reaction equation
[C:1](Cl)([CH3:3])=[O:2].[C:5]([SiH2:9][O:10][C:11]([CH3:23])([CH3:22])[C:12]1[CH:13]=[C:14]([CH2:19][CH2:20][NH2:21])[CH:15]=[CH:16][C:17]=1[Cl:18])([CH3:8])([CH3:7])[CH3:6].CCN(C(C)C)C(C)C.[NH4+].[Cl-]>C(Cl)Cl>[C:5]([SiH2:9][O:10][C:11]([CH3:23])([CH3:22])[C:12]1[CH:13]=[C:14]([CH2:19][CH2:20][NH:21][C:1](=[O:2])[CH3:3])[CH:15]=[CH:16][C:17]=1[Cl:18])([CH3:8])([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 137329923HCID 137329923, compound

Product 1

HCID 137329926HCID 137329926, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

AcCl (0.063 mL, 0.88 mmol) was added to a sol. of 2-[3-(tert-butyl-dimethyl-silanyloxymethyl)-4-chloro-phenyl]-ethylamine (252 mg, 0.840 mmol) and DIPEA (0.575 mL, 3.36 mmol) in CH2Cl2 (8.4 mL). The mixture was stirred at rt for 30 min, and aq. sat. NH4Cl was added. The layers were separated, and the org. layer was washed with aq. 1M NaOH, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC(CH2Cl2/MeOH 19:1) yielded the title compound (190 mg, 66%). LC-MS: tR=1.09 min; ES+: 342.19.

Workup

  1. customThe layers were separated
  2. washlayer was washed with aq. 1M NaOH
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the crude by FC(CH2Cl2/MeOH 19:1)

Sources & evidence

ORD record
ord-16f61c0f2dd041bbb6537c99aef7d61d
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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