Ethanol → 105355-26-8

HRID 1789169Notes

Reaction equation

HRID 1789169 reaction equation
Br[CH:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH3:24])=[CH:19][N:18]=2)=[CH:10][CH:9]=1)[C:3](OC)=[O:4].C([O-])(=O)C.[Na+].C(O)C.[NH2:33][C:34]([NH2:36])=[S:35]>>[CH2:23]([C:20]1[CH:21]=[CH:22][C:17]([CH2:16][CH2:15][O:14][C:11]2[CH:12]=[CH:13][C:8]([CH2:7][CH:2]3[S:35][C:34](=[NH:33])[NH:36][C:3]3=[O:4])=[CH:9][CH:10]=2)=[N:18][CH:19]=1)[CH3:24]

Participants

5

Reactant 4

HCID 702EthanolHCID 517045Sodium AcetateHCID 2723790ThioureaHCID 11610843Methyl 2-bromo-3-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}propanoate

Product 1

HCID 135905356105355-26-8Yield 523%

Procedure

A mixture of the crude oil of methyl 2-bromo-3-{4-[2-(5-ethyl-2-pyridyl)ethoxy]phenyl}propionate (73.0 g) obtained in (b) thiourea (14.2 g), sodium acetate (15.3 g) and ethanol (500 ml) was stirred for 3 hours under reflux. The reaction mixture was concentrated under reduced pressure, and the concentrate wasneutralized with a saturated aqueous solution of sodium hydrogencarbonate, to which were added water (200 ml) and ether (100 ml). The whole mixture was stirred for 10 minutes to yield 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2-imino-4-thiazolidinone as crystals (0.3 g, 523.0%). Recrystallization from methanol gave colorless prisms, m.p. 187°-188° C. (decomp.). Elemental analysis for C19H21N3O2S Calcd.: C, 64.20; H, 5.95; N, 11.82. Found: C, 64.20; H, 5.84; N, 11.73.

Workup

  1. temperatureunder reflux
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionwere added water (200 ml) and ether (100 ml)

Sources & evidence

ORD record
ord-c3fa941edf5d4f6885bf7cdb75cdc2c3
Source dataset
uspto-grants-1987_08
Patent number
US04687777

Reaction notes

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