Hydrochloric Acid → 3-{4-[4-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-pyridin-2-yl}-benzenesulfonic acid hydrochloride

HRID 1989264Notes

Reaction equation

HRID 1989264 reaction equation
CC(C)(C)C[O:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:19]=[C:18]([C:20]3[N:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[C:22]([C:30]4[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=4)[N:21]=3)[CH:17]=[CH:16][N:15]=2)[CH:9]=1)(=[O:7])=[O:6].[ClH:42]>O1CCOCC1>[ClH:42].[F:29][C:26]([F:27])([F:28])[C:24]1[CH:23]=[C:22]([C:30]2[CH:31]=[CH:32][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:34][CH:35]=2)[N:21]=[C:20]([C:18]2[CH:17]=[CH:16][N:15]=[C:14]([C:10]3[CH:9]=[C:8]([S:5]([OH:7])(=[O:6])=[O:4])[CH:13]=[CH:12][CH:11]=3)[CH:19]=2)[N:25]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 574688403-{4-[4-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-pyridin-2-yl}-benzenesulfonic acid 2,2-dimethyl-propyl ester

Product 1

HCID 574688413-{4-[4-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-pyridin-2-yl}-benzenesulfonic acid hydrochlorideYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A stirred mixture of 3-{4-[4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-pyridin-2-yl}-benzenesulfonic acid 2,2-dimethyl-propyl ester (1.27 g, 2.13 mmol), 37% HCl (12.5 ml) and dioxane (12.5 ml) was heated under reflux conditions for 19 h and evaporated to dryness. Diethyl ether (50 ml) was added to the crude product and the mixture was stirred at room temperature for 1 h. The precipitate was collected by filtration and dried to yield 3-{4-[4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-pyridin-2-yl}-benzenesulfonic acid hydrochloride as a white solid (1.08 g, 90%). MS (ISN) 524.0 [(M−H)−]; mp 407° C. (dec.).

Workup

  1. temperaturewas heated under reflux conditions for 19 h
  2. customevaporated to dryness
  3. additionDiethyl ether (50 ml) was added to the crude product
  4. filtrationThe precipitate was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-07303f2a85514a84bdb531f93501749a
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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