4-Methylmorpholine → HCID 54087737, compound

HRID 439828Notes

Reaction equation

HRID 439828 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11][CH2:12][C:13]([OH:15])=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].CN1CCOCC1.Cl.CN(C)CCCN=C=NCC.[F:35][C:36]1[C:41](O)=[C:40]([F:43])[C:39]([F:44])=[C:38]([F:45])[C:37]=1[F:46]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11][CH2:12][C:13]([O:15][C:41]2[C:40]([F:43])=[C:39]([F:44])[C:38]([F:45])=[C:37]([F:46])[C:36]=2[F:35])=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 13041PentafluorophenolHCID 72503895735-63-0HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 54087737HCID 54087737, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(3,4-dimethoxyphenylmercapto)ethanoic acid (1.71 g, 7.5 mmol), N-methylmorpholine (0.99 ml, 9.0 mmol), N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (1.87 g, 9.7 mmol) and pentafluorophenol (2.76 g, 15.0 mmol) in DCM (100 ml) was stirred at room temperature overnight. The solution was washed with 2M hydrochloric acid, saturated aqueous sodium hydrogen carbonate and brine, dried, filtered and concentrated to give crude pentafluorophenyl 2-(3,4-dimethoxyphenylmercapto)ethanoate (2.95 g, 99%) as pink oil which was used directly in the next step.

Workup

  1. washThe solution was washed with 2M hydrochloric acid, saturated aqueous sodium hydrogen carbonate and brine
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c04cbcec8f6c46229c30c57a40b4627a
Source dataset
uspto-grants-1996_05
Patent number
US05516783

Reaction notes

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