Sodium Hydroxide → HCID 11559214, compound

HRID 2074129Notes

Reaction equation

HRID 2074129 reaction equation
C(OC([C:6]1[S:7][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:28])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([F:27])([F:26])[F:25])[CH2:13][CH2:12]2)=[N:9][N:10]=1)=O)C.[OH-].[Na+]>C(O)C>[S:7]1[CH:6]=[N:10][N:9]=[C:8]1[N:11]1[CH2:12][CH2:13][N:14]([C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24]([F:27])([F:25])[F:26])=[O:28])[CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 115823885-[4-(2-Trifluoromethylbenzoyl)piperazin-1-YL]-[1,3,4]thiadiazole-2-carboxylic acid ethyl ester

Product 1

HCID 11559214HCID 11559214, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-[4-(2-Trifluoromethylbenzoyl)piperazin-1-yl][1,3,4]thiadiazole-2-carboxylic acid ethyl ester (0.828 g, 2.00 mmol) was added to 1 N NaOH in ethanol. The mixture was stirred for 3 hours and then evaporated to dryness. Water (10 mL) was added to the mixture, and pH of the solution was adjusted to 3 by the addition of 1 N HCl. The mixture was then extracted with ethyl acetate (2×50 mL). The combined organic phase was washed with brine, dried over anhydrous Na2SO4, then concentrated. The title compound was obtained as a white powder in 81% yield (0.552 g). 1H NMR (500 MHz, CDCl3) δ 8.52 (s, 1H), 7.74 (d, J=7.8 Hz, 1H), 7.63 (dd, J=7.5, 7.5 Hz, 1H), 7.57 (dd, J=7.5, 7.5 Hz, 1H), 7.35 (d, J=7.5 Hz, 1H), 4.02-4.08 (m, 1H), 3.88-3.93 (m, 1H), 3.60-3.66 (m, 2H), 3.54-3.58 (m, 2H), 3.33-3.37 (m, 2H). MS (ES+) m/z 343 (M+1).

Workup

  1. customevaporated to dryness
  2. additionWater (10 mL) was added to the mixture, and pH of the solution
  3. additionwas adjusted to 3 by the addition of 1 N HCl
  4. extractionThe mixture was then extracted with ethyl acetate (2×50 mL)
  5. washThe combined organic phase was washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d21cb40b691a4d6f887d5f990a0445c9
Source dataset
uspto-grants-2011_04
Patent number
US07919496B2

Reaction notes

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