p-Toluenesulfonic acid → HCID 68436651, compound

HRID 1853441

Reaction equation

HRID 1853441 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[CH3:10]OC(OC)N(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.Br.[CH2:30]([S:32][C:33](=[NH:35])[NH2:34])[CH3:31]>CN(C)C=O>[CH2:8]([O:7][C:1]([C:2]1[C:3]([CH3:5])=[N:35][C:33]([S:32][CH2:30][CH3:31])=[N:34][CH:10]=1)=[O:6])[CH3:9]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8868Ethyl AcetoacetateHCID 78373Dimethylformamide dimethyl acetalHCID 200213S-Ethylisothiuronium bromide

Product 1

HCID 68436651HCID 68436651, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl acetoacetate (6.37 mL, 50.0 mol), dimethylformamide dimethylacetal (8.94 g, 75.0 mmol), and catalytic p-toluenesulfonic acid was heated at 100° C. for 2 h. After cooling to rt, the mixture was diluted with N,N-dimethylformamide (DMF; 50 mL) and 2-ethylisothiourea hydrobromide (9.10 g, 50.0 mmol) was added. After heating the at 100° C. for 18 h, the mixture was cooled to rt and concentrated to give a crude residue, which was purified by FCC (EtOAc/hexanes) to give 7.1 g (61%) of a solid. 1H NMR (CDCl3): 8.97-8.91 (m, 1H), 4.43-4.35 (m, 2H), 3.24-3.15 (m, 2H), 2.81-2.72 (m, 3H), 1.47-1.35 (m, 6H).

Workup

  1. temperatureAfter cooling to rt
  2. additionwas added
  3. temperatureAfter heating the at 100° C. for 18 h
  4. temperaturethe mixture was cooled to rt
  5. concentrationconcentrated
  6. customto give a crude residue, which
  7. customwas purified by FCC (EtOAc/hexanes)

Sources & evidence

ORD record
ord-4a97bec3cc0c435d9193e78165c0e87a
Source dataset
uspto-grants-2015_02
Patent number
US08962644B2

Linked notes

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