Water → HCID 178517925, compound

HRID 1246783Notes

Reaction equation

HRID 1246783 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[C:4]([NH:6][C:7]1[C:8](Cl)=[N:9][CH:10]=[N:11][C:12]=1[NH:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)=O.[OH:26]S(O)(=O)=O.O>C(O)(C)C>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([N:13]2[C:4]([C:3]3[CH:22]=[CH:23][CH:24]=[CH:25][C:2]=3[Cl:1])=[N:6][C:7]3[C:12]2=[N:11][CH:10]=[N:9][C:8]=3[OH:26])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 167263122-Chloro-N-[4-chloro-6-(4-chlorophenylamino)-pyrimidin-5-yl]-benzamide

Product 1

HCID 178517925HCID 178517925, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a suspension of 2-chloro-N-[4-chloro-6-(4-chlorophenylamino)-pyrimidin-5-yl]-benzamide I-(4A-7)a (1.00 g, 2.54 mmol) in isopropanol (20 ml) was added neat H2SO4 (410 μl, 7.4 mmol) at room temperature. The reaction was refluxed for 8 hours followed by cooling to room temperature and stirring for 16 hr. To the heterogeneous solution was added 20 ml of water to promote further product precipitation. After stirring for 1 an additional hour at room temperature, the solid was collected on a sintered glass funnel, rinsing with water followed by hexanes. The product was further dried under reduced pressure to give I-(4A-7)b as a colorless solid (0.72 g, 80%): 1H NMR: (400 MHz, DMSO-d6): δ 12.57 (s, 1H), 8.08 (d, J=4.1 Hz, 1 H), 7.66 (dd, J=7.4, 1.2 Hz, 1H), 7.51–7.41 (m, 5H), 7.33–7.29 (m, 2H).

Workup

  1. temperatureThe reaction was refluxed for 8 hours
  2. customproduct precipitation
  3. stirringAfter stirring for 1 an additional hour at room temperature
  4. customthe solid was collected on a sintered glass funnel
  5. washrinsing with water
  6. customThe product was further dried under reduced pressure

Sources & evidence

ORD record
ord-9bead1f6f81746dda914c495707f5af8
Source dataset
uspto-grants-2006_10
Patent number
US07129239B2

Reaction notes

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