Sulfuric Acid → 3-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-4,5-dihydro-1H-pyrazole-5-carboxamide

HRID 448817Notes

Reaction equation

HRID 448817 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH:11]2[N:15]([C:16]3[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][N:17]=3)[N:14]=[C:13](C3C([N+]([O-])=O)=C(S([O-])(=O)=O)C=CC=3)[CH2:12]2)=[O:10])=[C:4]([C:36](=[O:43])[NH:37][CH:38]([CH:40]2[CH2:42][CH2:41]2)[CH3:39])[CH:3]=1.[Br-:44].[Na+].S(=O)(=O)(O)O.[OH-].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH:11]2[N:15]([C:16]3[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][N:17]=3)[N:14]=[C:13]([Br:44])[CH2:12]2)=[O:10])=[C:4]([C:36](=[O:43])[NH:37][CH:38]([CH:40]2[CH2:42][CH2:41]2)[CH3:39])[CH:3]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 253881Sodium BromideHCID 867619275-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenylcarbamoyl)-1-(3-chloropyridin-2-yl)-4,5-dihydro-1H-pyrazol-3-yl2-nitrobenzene sulfonate

Product 1

HCID 441856063-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-4,5-dihydro-1H-pyrazole-5-carboxamideYield 102.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

10.0 g of 5-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenylcarbamoyl)-1-(3-chloropyridin-2-yl)-4,5-dihydro-1H-pyrazol-3-yl2-nitrobenzene sulfonate was dissolved in 30 mL of acetic acid, and after adding 2.4 g of sodium bromide, 1.3 mL of 98 mass % concentrated sulfuric acid was dropwise added at room temperature. After completion of the dropwise addition, heating was carried out at an internal temperature of from 40 to 50° C. for about two hours. After completion of the reaction, the reaction solution was dropwise added into 60 mL of a 8 mass % sodium hydroxide aqueous solution to obtain 8.3 g of the desired product in a crystal form.

Workup

  1. additionwas dropwise added at room temperature
  2. additionAfter completion of the dropwise addition
  3. temperatureheating
  4. customAfter completion of the reaction

Sources & evidence

ORD record
ord-2ec6355d58674578a4b96c85413d5a99
Source dataset
uspto-grants-2013_07
Patent number
US08481744B2

Reaction notes

Loading…