Diisopropylethylamine → HCID 178518168, compound

HRID 1620653Notes

Reaction equation

HRID 1620653 reaction equation
S=[C:2]1[CH2:6][S:5][C:4](=[O:7])[NH:3]1.Cl.[NH2:9][C@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[OH:16].C(N(C(C)C)C(C)C)C>C(O)C>[OH:16][C@H:11]1[CH2:12][CH2:13][CH2:14][CH2:15][C@H:10]1[NH:9][C:2]1[CH2:6][S:5][C:4](=[O:7])[N:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 15395954-Sulfanylidene-1,3-thiazolidin-2-oneHCID 12228413(1R,2S)-2-aminocyclohexan-1-ol hydrochloride

Product 1

HCID 178518168HCID 178518168, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-thioxo-1,3-thiazolidin-2-one (870 mg) in ethanol (30 mL) were added cis-2-aminocyclohexanol hydrochloride (1.00 g) and N-ethyl-N-(1-methylethyl)propan-2-amine (2.32 mL), and the mixture was heated under reflux overnight. The reaction mixture was concentrated under reduced pressure, the residue was purified by silica gel column chromatography (methanol/ethyl acetate), and the obtained powder was washed with ethyl acetate to give the title compound (504 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (methanol/ethyl acetate)
  5. washthe obtained powder was washed with ethyl acetate

Sources & evidence

ORD record
ord-e63e5e2a7c6144bb9a888bcec615a562
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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