Sodium Hydroxide → HCID 178515324, compound

HRID 627472

Reaction equation

HRID 627472 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.[F:12][C:13]([F:24])([F:23])[C:14](=O)[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[OH-].[Na+].[NH4+].[OH-]>C(Cl)Cl>[I:11][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][CH:9]=1)[N:1]=[C:14]([C:13]([F:23])([F:24])[F:12])[C:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[C:4]2[OH:6]

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 72911Benzoic acid, 2-amino-5-iodo-HCID 2229581,1,1-Trifluoro-3-phenyl-2-propanone2×HCID 86584057Phosphorus Pentoxide-Methanesulfonic Acid

Product 1

HCID 178515324HCID 178515324, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-amino-5-iodobenzoic acid (5.20 g, 19.8 mmol), 1,1,1-trifluoro-3-phenylpropan-2-one (3.95 g, 21.0 mmol), and Eaton's reagent (12 mL) in a sealed tube was heated at 100° C. for 2 hours. More 1,1,1-trifluoro-3-phenylpropan-2-one (1.60 g, 8.50 mmol) was added and the mixture was heated for another 2 hours. The reaction was then cooled to room temperature, ice water was added, and the mixture was stirred vigorously for about 20 min. 50% NaOH and conc. NH4OH solution were added until pH was 9. Some gummy dark brown material formed. After the addition of CH2Cl2, the gummy material became fluffy solid. This solid was filtered, washed with water and Et2O, and air dried to give the title compound.

Workup

  1. temperaturethe mixture was heated for another 2 hours
  2. temperatureThe reaction was then cooled to room temperature
  3. customSome gummy dark brown material formed
  4. filtrationThis solid was filtered
  5. washwashed with water and Et2O, and air
  6. customdried

Sources & evidence

ORD record
ord-1929ab8ba3eb4739a08d589c4e9fc9ad
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Linked notes

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