Sulfuric Acid → HCID 136410984, compound

HRID 1626316Notes

Reaction equation

HRID 1626316 reaction equation
Cl[C:2]1[C:7]([NH:8][C:9](=O)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:5]=[CH:4][N:3]=1.S(=O)(=O)(O)[OH:25].C([O-])(O)=O.[Na+]>CC(O)C>[C:10]1([C:9]2[N:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:6]3[N:5]=[CH:4][NH:3][C:2](=[O:25])[C:7]=3[N:8]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 86670632HCID 86670632, compound

Product 1

HCID 136410984HCID 136410984, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of N-(4-chloro-6-(phenylamino)pyrimidin-5-yl)benzamide obtained in step 2 (35 g, 108 mmol) in 2-propanol (360 mL) was added sulfuric acid (18.2 mL, 323.3 mmol) at 0° C. The reaction mixture was heated to reflux at 90° C. overnight. After cooled to room temperature NaHCO3 (aq) was added to the resulting reaction mixture and stirred. The resulting mixture was filtered with water (600 mL). The collected solid was dried under reduced pressure to obtain the title compound (22.3 g, 72%) as white solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. additionwas added to the resulting reaction mixture
  3. filtrationThe resulting mixture was filtered with water (600 mL)
  4. customThe collected solid was dried under reduced pressure

Sources & evidence

ORD record
ord-8ace9524f97240979c1dd2991e8a99b2
Source dataset
uspto-grants-2014_07
Patent number
US08785453B2

Reaction notes

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