Lithium → HCID 178524836, compound

HRID 872607Notes

Reaction equation

HRID 872607 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[S:7][CH:8]=[C:9]([C:11]([O:13]CC)=[O:12])[N:10]=2)[N:3]=[CH:2]1.[Li]>C1COCC1>[NH:1]1[CH:5]=[C:4]([C:6]2[S:7][CH:8]=[C:9]([C:11]([OH:13])=[O:12])[N:10]=2)[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 3028194Lithium2×HCID 178470099HCID 178470099, compound

Product 1

HCID 178524836HCID 178524836, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-(1H-imidazol-4-yl)thiazole-4-carboxylate (1.5 g, 6.72 mmol) was dissolved in THF (10 ml). Into the suspension, lithium hydroxyde monohydrate 1M solution (13.44 ml, 13.44 mmol) was added and the resulting mixture was stirred for 4 h. Then 3.36 ml of lithium hydroxyde monohydrate 1M solution was added and the mixture was stirred for another hour. The mixture was evaporated, 10 ml of water added and the pH was adjusted to 1 with concentrated HCl. The precipitate was filtered. Both the filtrate and filtered precipitate contained the product. The filtrate was dissolved in toluene and evaporated twice. LC-MS: [M+1]=196.20.

Workup

  1. stirringthe mixture was stirred for another hour
  2. customThe mixture was evaporated
  3. addition10 ml of water added
  4. filtrationThe precipitate was filtered
  5. filtrationBoth the filtrate and filtered precipitate
  6. dissolutionThe filtrate was dissolved in toluene
  7. customevaporated twice

Sources & evidence

ORD record
ord-8cbe97b634474d5190cdb9c779e2901f
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

Loading…