Trichloroacetyl chloride → HCID 59432914, compound

HRID 507239Notes

Reaction equation

HRID 507239 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-ac0712c477d04e709ea57f6f98ce543d
Source dataset
uspto-grants-2010_08
Patent number
US07786137B2

Reaction notes

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