p-(Trifluoromethoxy)phenyl isocyanate → HCID 21062339, compound

HRID 268613Notes

Reaction equation

HRID 268613 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]=[O:12])=[CH:6][CH:5]=1.[NH2:15][CH:16]([CH:32]([CH3:34])[CH3:33])[C:17]([N:19]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])=[O:18]>ClCCl>[CH2:25]([N:19]([CH2:20][CH2:21][N:22]([CH3:23])[CH3:24])[C:17](=[O:18])[C@@H:16]([NH:15][C:11]([NH:10][C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:13])([F:14])[F:1])=[CH:9][CH:8]=1)=[O:12])[CH:32]([CH3:33])[CH3:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 92298p-(Trifluoromethoxy)phenyl isocyanateHCID 21938687HCID 21938687, compound

Product 1

HCID 21062339HCID 21062339, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(Trifluoromethoxy)phenyl isocyanate (0.18 g, 0.86 mmole) was slowly added to a solution of 13 (0.20 g, 0.72 mmole) in dichloromethane (20 mL) at 0° C. The solution was allowed to warm to room temperature and stirred for 18 h. The reaction was then quenched with water (20 mL), and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated by rotary evaporation. The organic residue was purified by flash chromatographey on silica gel, eluting with dichloromethane/2.0 M ammonia in ethyl alcohol (96:4) to give 14a (0.24 g, 69%) as a white solid; MS (EI)=480 (M+).

Workup

  1. customThe reaction was then quenched with water (20 mL)
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporation
  5. customThe organic residue was purified by flash chromatographey on silica gel
  6. washeluting with dichloromethane/2.0 M ammonia in ethyl alcohol (96:4)

Sources & evidence

ORD record
ord-605435a95f254464a4a25763f17a3d8e
Source dataset
uspto-grants-2008_11
Patent number
US07446115B2

Reaction notes

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