Ammonia → HCID 66571316, compound

HRID 1403217Notes

Reaction equation

HRID 1403217 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:23])=[C:6]([C:8]2[NH:9][C:10]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:21][CH3:22])[N:16]=3)=[CH:11][C:12]=2[C:13]#[N:14])[CH:7]=1.O.S(=O)(=O)(O)[OH:26].N>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:23])=[C:6]([C:8]2[NH:9][C:10]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:21][CH3:22])[N:16]=3)=[CH:11][C:12]=2[C:13]([NH2:14])=[O:26])[CH:7]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962Water2×HCID 1118Sulfuric AcidHCID 70980124HCID 70980124, compound

Product 1

HCID 66571316HCID 66571316, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-(5-chloro-2-methyl-phenyl)-5-(2-methylamino-pyrimidin-4-yl)-1H-pyrrole-3-carbonitrile (1.15 g, 3.55 mmol) in TFA (15.0 mL) were sequentially added water (2.25 mL) and 98% sulfuric acid (4.5 mL) under efficient stirring. The mixture was allowed to stir for 8 h at 70° C. and then was diluted by drop wise addition of water (45 mL). The reaction mixture was made basic (pH 10-12) by adding 30% aqueous ammonia (15 mL) under stirring. The precipitated solid was collected by filtration, washed with water and finally dried in a vacuum oven at 50° C. affording the title compound as an off-white solid (1.07 g, 88%).

Workup

  1. stirringunder stirring
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with water
  4. customfinally dried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-0cf6313d5b444429b4a965bad9e2b366
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

Loading…