Trichloroacetyl chloride → HCID 59432914, compound

HRID 1809338Notes

Reaction equation

HRID 1809338 reaction equation
[Cl:1][C:2]([Cl:7])([Cl:6])[C:3](Cl)=[O:4].[CH2:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][NH:9]1.CCN(CC)CC>C(Cl)Cl>[Cl:1][C:2]([Cl:7])([Cl:6])[C:3]([N:9]1[CH2:10][C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8]1)=[O:4]

Participants

5

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 422478Isoindoline

Product 1

HCID 59432914HCID 59432914, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under N2, at 0° C., trichloroacetyl chloride (0.57 mL, 5.0 mmol) was added dropwise to a stirring solution of isoindoline (1.0 g, 5.0 mmol), Et3N (0.7 mL, 0.51 g, 5.0 mmol) and CH2Cl2 (20 mL). The solution was allowed to warm to room temperature and stirred for 1 h. After evaporating the solvents in vacuo, the mixture was purified via silica gel chromatography using 8:2 hexanes/EtOAc to obtain the desired amide (1.2 g, 4.6 mmol, 91% yield). LC/MS (10-99% CH3CN), M/Z: M+1 obs=265.9; tR=3.51 min.

Workup

  1. customAfter evaporating the solvents in vacuo
  2. customthe mixture was purified via silica gel chromatography

Sources & evidence

ORD record
ord-75f7cf39c7e24a359e81910b8d0e5d21
Source dataset
uspto-grants-2013_01
Patent number
US08362032B2

Reaction notes

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