Trichloroacetyl chloride → HCID 10181527, compound

HRID 1266469Notes

Reaction equation

HRID 1266469 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[NH2:20])[C:5]2[O:10][CH2:9][O:8][CH2:7][C:6]=2[CH:11]=1.C(N(CC)C(C)C)(C)C.[Cl:30][C:31]([Cl:36])([Cl:35])[C:32](Cl)=[O:33]>O1CCCC1>[Cl:30][C:31]([Cl:36])([Cl:35])[C:32]([NH:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[O:13][CH2:12][C:4]1[C:5]2[O:10][CH2:9][O:8][CH2:7][C:6]=2[CH:11]=[C:2]([Cl:1])[CH:3]=1)=[O:33]

Participants

5

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 9922087HCID 9922087, compound

Product 1

HCID 10181527HCID 10181527, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[(6-chloro-2H,4H-benzo[e]1,3-dioxin-8-yl)methoxy]phenylamine (75 mg, 0.257 mmol) in anhydrous tetrahydrofuran (2 mL) was added N,N-diisopropylethylamine (0.090 mL, 0.514 mmol), followed by trichloroacetyl chloride (0.058 mL, 0.514 mmol). The resulting mixture was stirred at room temperature for 16 hours. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography to give 2,2,2-trichloro-N-{2-[(6-chloro(2H,4H-benzo[e]1,3-dioxin-8-yl))methoxy]phenyl}acetamide, M+1=438.1.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-6df644783d594f7ba399e8ef5582ff44
Source dataset
uspto-grants-2003_04
Patent number
US06548548B2

Reaction notes

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