6-Isocyanato-2,2,4,4-tetrefluoro-1,3-benzodioxene → HCID 59987451, compound

HRID 658495Notes

Reaction equation

HRID 658495 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=2)[CH:8]=[CH:7][N:6]=1)=[O:4].[CH:19]1[C:24]([N:25]=[C:26]=[O:27])=[CH:23][C:22]2[C:28]([F:35])([F:34])[O:29][C:30]([F:33])([F:32])[O:31][C:21]=2[CH:20]=1>C(Cl)Cl>[CH3:1][NH:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:18]=[CH:17][C:15]([NH:16][C:26]([NH:25][C:24]3[CH:19]=[CH:20][C:21]4[O:31][C:30]([F:33])([F:32])[O:29][C:28]([F:34])([F:35])[C:22]=4[CH:23]=3)=[O:27])=[CH:14][CH:13]=2)[CH:8]=[CH:7][N:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 27752076-Isocyanato-2,2,4,4-tetrefluoro-1,3-benzodioxeneHCID 166551294-(4-Aminophenoxy)-N-methylpicolinamide

Product 1

HCID 59987451HCID 59987451, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a slurry of 4-(2-(N-methylcarbamoyl)-4-pyridyloxy)aniline (143 mg, 0.59 mmol) in DCM (1 mL) at 0° C. was added dropwise a solution of 2,2,4,4-tetrafluoro-6-isocyanato-1,3-benzodioxene (150 mg, 0.60 mmol) in DCM (1 mL). The reaction mixture was stirred at room temperature for 12 h. The resulting precipitate was filtered and washed with DCM to afford the desired product (125 mg, 41%) as a white solid.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with DCM

Sources & evidence

ORD record
ord-3f7e4ff1edf94c25b6542cbe987bf224
Source dataset
uspto-grants-2011_12
Patent number
US08076488B2

Reaction notes

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