Diglycolamine → HCID 178518154, compound

HRID 1620479Notes

Reaction equation

HRID 1620479 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][OH:7].S=[C:9]1[CH2:13][S:12][C:11](=[O:14])[NH:10]1.[F:15][C:16]([F:37])([F:36])[C:17]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][C:18]=1[CH2:19][N:20]1[CH2:25][CH2:24][CH:23]([CH:26]=O)[CH2:22][CH2:21]1.CC(C)([O-])C.[K+].[Cl-].[NH4+]>C(O)C.C(OCC)(=O)C>[F:37][C:16]([F:15])([F:36])[C:17]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][C:18]=1[CH2:19][N:20]1[CH2:25][CH2:24][CH:23](/[CH:26]=[C:13]2/[C:9]([NH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][OH:7])=[N:10][C:11](=[O:14])[S:12]/2)[CH2:22][CH2:21]1

Participants

8

Reactant 5

HCID 13578DiglycolamineHCID 25517Ammonium ChlorideHCID 15395954-Sulfanylidene-1,3-thiazolidin-2-oneHCID 23665647Potassium tert-butoxideHCID 866786631-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde

Product 1

HCID 178518154HCID 178518154, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(2-aminoethoxy)ethanol (4.24 mL) in ethanol (30 mL) was added 4-thioxo-1,3-thiazolidin-2-one (5.65 g), and the mixture was stirred at room temperature for 4 hr. To the reaction mixture were added 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (12 g) and potassium tert-butoxide (4.76 g), and the mixture was stirred at 80° C. for 3 hr. The reaction mixture was cooled to room temperature, saturated aqueous ammonium chloride solution/ethyl acetate were added, and the organic layer was separated, washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate) to give the title compound (4.3 g).

Workup

  1. stirringthe mixture was stirred at 80° C. for 3 hr
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customthe organic layer was separated
  4. washwashed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (methanol/ethyl acetate)

Sources & evidence

ORD record
ord-4e1b1eeb1ab54c96af950616e8c0fa15
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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