Lithium hydroxide, monohydrate → HCID 57875803, compound

HRID 1665643Notes

Reaction equation

HRID 1665643 reaction equation
O[Li].O.C([O:6][C:7](=[O:23])[CH2:8][C:9]([NH:11][C:12]1[S:13][CH:14]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:16]=1)=[O:10])C>CO.C1COCC1.O>[C:17]1([C:15]2[N:16]=[C:12]([NH:11][C:9](=[O:10])[CH2:8][C:7]([OH:23])=[O:6])[S:13][CH:14]=2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 21856677HCID 21856677, compound

Product 1

HCID 57875803HCID 57875803, compoundYield 87.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH.H2O (85 mg, 2.0 mmol) was added to a solution of N-(4-phenyl-thiazol-2-yl)-malonamic acid ethyl ester (292 mg, 1.0 mmol) in methanol (1.0 mL), THF (1.5 mL) and H2O (1 mL). The resulting mixture was stirred for 1 hour at room temperature then concentrated. The residue was diluted with water, acidified with concentrated HCl and extracted with ethyl acetate. The organics were washed with brine, dried over Na2SO4 and concentrated to afford 230 mg (87%) of N-(4-Phenyl-thiazol-2-yl)-malonamic acid.

Workup

  1. concentrationthen concentrated
  2. additionThe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe organics were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-664b9e2215d5410cb52558e2643554aa
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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