Hydrochloric Acid → HCID 45420167, compound

HRID 1013059Notes

Reaction equation

HRID 1013059 reaction equation
Cl.[F:2][C:3]([F:17])([F:16])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:5]=1.C([O-])(O)=O.[Na+].Cl[S:24]([C:27]1[CH:32]=[CH:31][C:30]([CH:33]=[CH:34][C:35]([OH:37])=[O:36])=[CH:29][CH:28]=1)(=[O:26])=[O:25].Cl>O1CCOCC1.O>[F:17][C:3]([F:2])([F:16])[C:4]1[CH:5]=[C:6]([N:10]2[CH2:15][CH2:14][N:13]([S:24]([C:27]3[CH:28]=[CH:29][C:30](/[CH:33]=[CH:34]/[C:35]([OH:37])=[O:36])=[CH:31][CH:32]=3)(=[O:26])=[O:25])[CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 3084246TFMPP hydrochlorideHCID 38309693-(4-Chlorosulfonyl-phenyl)-acrylic acid

Product 1

HCID 45420167HCID 45420167, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 1-(α,α,α-trifluoro-m-tolyl)piperazine hydrochloride (0.43 g, 1.62 mmol) in dioxane (5 mL) a solution of NaHCO3 (0.27 g, 3.24 mmol) in water (4 mL) and a solution of 3-(4-chlorosulfonyl-phenyl)-acrylic acid (8) (0.40 g, 1.62 mmol) were added and the resultant mixture was stirred at ambient temperature for 20 hours. The reaction mixture was poured into water (50 mL) and the pH of the medium was brought to ˜4 with 2 N HCl. The precipitated solid was filtered, washed with water, and dried in vacuum to give the title compound (0.59 g, 82%). 1H NMR (DMSO-d6, HMDSO), δ: 2.96-3.67 (8H, m, overlapped with a signal of water); 6.74 (1H, d, J=16.3 Hz); 7.01-7.57 (4H, m); 7.67 (1H, d, J=16.3 Hz); 7.82 (2H, d, J=8.4 Hz); 8.00 (2H, d, J=8.4 Hz); 12.71 (1H, br s).

Workup

  1. filtrationThe precipitated solid was filtered
  2. washwashed with water
  3. customdried in vacuum

Sources & evidence

ORD record
ord-9de965ac39eb42adb8d12a849f57709d
Source dataset
uspto-grants-2011_07
Patent number
US07981895B2

Reaction notes

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