Isopropanol → HCID 86667467, compound

HRID 2401862Notes

Reaction equation

HRID 2401862 reaction equation
Br[CH:2]([C:8](=O)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(O)(C)C.[NH2:22][C:23]([NH2:25])=[S:24]>>[NH2:25][C:23]1[S:24][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[N:22]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 2723790ThioureaHCID 86667466HCID 86667466, compound

Product 1

HCID 86667467HCID 86667467, compoundYield 99%

Procedure

In a 100 mL round bottomed flask, to a solution of ethyl 2-bromo-4-(4-chlorophenyl)-3-oxobutanoate (990 mg, 3.1 mmol) in isopropyl alcohol (20 mL, 300 mmol) was added thiourea (590 mg, 7.8 mmol) and the resulting mixture was stirred at reflux for 16 hours. The mixture was allowed to cool to room temperature and then concentrated under reduced pressure. The residue was suspended in EtOAc (50 mL) and then washed with a saturated aqueous solution of NaHCO3 (50 mL), brine (50 mL). The resulting organic layer was dried over anhydrous MgSO4, filtered, and concentrated to afford ethyl 2-amino-4-(4-chlorobenzyl)-1,3-thiazole-5-carboxylate (900 mg, yield >99%) as a yellowish solid that was used without further purification. LC/MS (FA) ES+ 297, 299.

Workup

  1. temperatureat reflux for 16 hours
  2. concentrationconcentrated under reduced pressure
  3. washwashed with a saturated aqueous solution of NaHCO3 (50 mL), brine (50 mL)
  4. dry with materialThe resulting organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7ce9763c98554f9bbbb996347327c5f1
Source dataset
uspto-grants-2014_08
Patent number
US08796268B2

Reaction notes

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