2-(Diethylamino)ethanethiol → 3'-[4-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-biphenyl-3-sulfonic acid

HRID 1989267Notes

Reaction equation

HRID 1989267 reaction equation
CC(C)(C)C[O:4][S:5]([C:8]1[CH:9]=[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([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:15]=2)[CH:11]=[CH:12][CH:13]=1)(=[O:7])=[O:6].C([O-])CC.[Na+].C(N(CC)CCS)C>O1CCOCC1>[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:16]2[CH:15]=[C:14]([C:10]3[CH:11]=[CH:12][CH:13]=[C:8]([S:5]([OH:7])(=[O:6])=[O:4])[CH:9]=3)[CH:19]=[CH:18][CH:17]=2)[N:25]=1

Participants

5

Reactant 3

HCID 160322-(Diethylamino)ethanethiolHCID 236693631-Propanol, sodium salt (1:1)HCID 574688443'-[4-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-biphenyl-3-sulfonic acid 2,2-dimethyl-propyl ester

Product 1

HCID 574688453'-[4-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-biphenyl-3-sulfonic acidYield 72.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A stirred mixture of 3′-[4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-biphenyl-3-sulfonic acid 2,2-dimethyl-propyl ester (1.42 g, 2.39 mmol), 2M sodium propanolate solution (3 ml, 6 mmol), 2-(diethylamino)-ethanethiol (0.37 g, 2.75 mmol) and dioxane (15 ml) was heated under reflux conditions for 24 h and evaporated. Water (40 ml) was added and the mixture was extracted with ethyl acetate (2×50 ml). The combined organic layers were washed with water (50 ml). The water layers were combined, acidified with 2N HCl and extracted with ethyl acetate (2×50 ml). The latter two organic layers were combined, washed with brine (50 ml), dried (MgSO4) and evaporated to yield the crude 3′-[4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-biphenyl-3-sulfonic acid as a brown solid (0.91 g, 51%). Thionyl chloride (20 ml) and DMF (4 drops) were added and the stirred mixture was heated under reflux conditions for 4 h, evaporated and purified by flash chromatography on silica gel (ethyl acetate/heptane) to yield the title compound as a light brown solid (0.43 g, 33%). MS (ISP) 542.2 [(M)+]; mp 176° C.

Workup

  1. temperaturewas heated under reflux conditions for 24 h
  2. customevaporated
  3. additionWater (40 ml) was added
  4. extractionthe mixture was extracted with ethyl acetate (2×50 ml)
  5. washThe combined organic layers were washed with water (50 ml)
  6. extractionextracted with ethyl acetate (2×50 ml)
  7. washwashed with brine (50 ml)
  8. dry with materialdried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-e19054ff096149b6994b237b4eec212b
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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