Benzaldehyde, 3-amino- → HCID 87362302, compound

HRID 1668336

Reaction equation

HRID 1668336 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=1[N:21]=[C:22]=[O:23].S([O-])(O)(=O)=O.[K+]>ClCCCl>[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=1[NH:21][C:22]([NH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([CH:5]=[O:6])[CH:3]=1)=[O:23]

Participants

5

Reactant 3

HCID 74366Benzaldehyde, 3-amino-HCID 516920Potassium bisulfateHCID 27333802-Fluoro-5-(trifluoromethyl)phenyl isocyanate

Product 1

HCID 87362302HCID 87362302, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 484 mg of 3-aminobenzaldehyde (4 mmol) (polymerized form) and 290 μl of 2-fluoro-5-trifluoromethylphenyl isocyanate in 4 ml of DCE is treated in a CEM Discover microwave oven at 100° C. for 10 minutes (power 90). After cooling, the mixture is poured into 100 ml of saturated potassium hydrogen sulfate solution and extracted with twice 50 ml of ethyl acetate. The combined organic phases are washed with water, dried over sodium sulfate and evaporated. 740 mg of the expected aldehyde (yield=57%) are obtained in an LC/MS purity of 82%. The crude product is used directly for the following steps. ([M+H]+): 327. RT=4.28 min (acetonitrile/water gradient from 30% to 90%—Method B).

Workup

  1. additionis treated in a CEM Discover microwave oven at 100° C. for 10 minutes (power 90)
  2. temperatureAfter cooling
  3. extractionextracted with twice 50 ml of ethyl acetate
  4. washThe combined organic phases are washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-4d5d4efd8a634b739b97bb363588779b
Source dataset
uspto-grants-2011_08
Patent number
US07989439B2

Linked notes

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