2-Bromophenyl isocyanate → HCID 18536716, compound

HRID 412074Notes

Reaction equation

HRID 412074 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[CH:5][N:6]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][C:17]=2[C:18]([F:21])([F:20])[F:19])[NH:14][C:13](=[O:22])[C:12]([C:23]([O:25]CC)=[O:24])=[CH:11]3)[CH:7]=1.[Br:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[N:35]=[C:36]=[O:37]>C(OCC)(=O)C>[Br:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[NH:35][C:36]([O:1][CH2:2][C:3]1[N:4]=[CH:5][N:6]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][C:17]=2[C:18]([F:21])([F:20])[F:19])[NH:14][C:13](=[O:22])[C:12]([C:23]([OH:25])=[O:24])=[CH:11]3)[CH:7]=1)=[O:37]

Participants

4

Reactant 2

HCID 1370972-Bromophenyl isocyanateHCID 9951850HCID 9951850, compound

Product 1

HCID 18536716HCID 18536716, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of the compound of Example 17 (100 mg, 262 μmol) in ethyl acetate (3 ml) was added 2-bromophenyl isocyanate (104 mg, 524 μmol), and the mixture was refluxed for 24 hours. After cooling, the precipitated crystals were collected by filtration, washed with ethyl acetate, and then dried under reduced pressure. These were suspended into ethanol (3 ml), 1 mol/L aqueous solution of lithium hydroxide (903 μl) and successively water (3 ml) were added, and the mixture was stirred for 75 minutes at 50° C. Ice water was added to the reaction mixture, the insolubles were filtered off. then the pH value was brought to 4 with 3 mol/L hydrochloric acid. The precipitated crystals were collected by filtration, washed with water, and then dried under reduced pressure, thereby obtaining 55.0 mg of title compound as colorless powder. Yield 34%.

Workup

  1. temperaturethe mixture was refluxed for 24 hours
  2. temperatureAfter cooling
  3. filtrationthe precipitated crystals were collected by filtration
  4. washwashed with ethyl acetate
  5. customdried under reduced pressure
  6. additionwere added
  7. additionIce water was added to the reaction mixture
  8. filtrationthe insolubles were filtered off
  9. filtrationThe precipitated crystals were collected by filtration
  10. washwashed with water
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-df791749f40143f4886481a161cc635c
Source dataset
uspto-grants-2003_05
Patent number
US06562839B1

Reaction notes

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