Thiourea → HCID 86668388, compound

HRID 529747Notes

Reaction equation

HRID 529747 reaction equation
Br[CH:2]([C:8]([C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[O:17][CH3:18])=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:19][C:20]([NH2:22])=[S:21]>C(O)C>[NH2:22][C:20]1[S:21][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:8]([C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[O:17][CH3:18])[N:19]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 86668389HCID 86668389, compound

Product 1

HCID 86668388HCID 86668388, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 2-bromo-3-(5-chloro-2-methoxyphenyl)-3-oxopropanoate (assumed to be 13.2 mmol) and thiourea (1.01 g, 13.3 mmol) in ethanol (25 mL) were heated to reflux for 3 hours, then cooled to room temperature for 18 hours. The resultant solid was removed by filtration and the filtrate evaporated under vacuum. DCM was added to the residue, the organics washed with sodium hydrogen carbonate (sat.aq.), water and brine, and evaporated to dryness. The residue was triturated (DCM) to give ethyl 2-amino-4-(5-chloro-2-methoxyphenyl)thiazole-5-carboxylate (1.30 g, 31%) as a yellow solid. LCMS (method 1) [M+H]+=313.2, RT=3.15 min. 1H NMR (400 MHz, DMSO-d6): δ (ppm) 7.77 (s, br, 2H), 7.39 (dd, 1H), 7.22 (d, 1H), 7.05 (d, 1H), 4.00 (q, 2H), 3.70 (s, 3H), 1.04 (t, 3H).

Workup

  1. temperaturewere heated
  2. temperatureto reflux for 3 hours
  3. customThe resultant solid was removed by filtration
  4. customthe filtrate evaporated under vacuum
  5. additionDCM was added to the residue
  6. washthe organics washed with sodium hydrogen carbonate (sat.aq.), water and brine
  7. customevaporated to dryness
  8. customThe residue was triturated (DCM)

Sources & evidence

ORD record
ord-e248018f780946e49e10a05aecde66e5
Source dataset
uspto-grants-2016_05
Patent number
US09346815B2

Reaction notes

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