Diethyl Malonate → HCID 178516644, compound

HRID 530737Notes

Reaction equation

HRID 530737 reaction equation
CC[O-].[Na+].Cl.[F:6][C:7]([F:17])([F:16])[C:8]1[N:9]=[C:10]([C:13]([NH2:15])=[NH:14])[S:11][CH:12]=1.[C:18](OCC)(=[O:25])[CH2:19][C:20](OCC)=[O:21]>CCO>[F:17][C:7]([F:6])([F:16])[C:8]1[N:9]=[C:10]([C:13]2[N:15]=[C:20]([OH:21])[CH:19]=[C:18]([OH:25])[N:14]=2)[S:11][CH:12]=1

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 2723922Sodium ethoxideHCID 667304744-(Trifluoromethyl)thiazole-2-carboximidamide hydrochloride

Product 1

HCID 178516644HCID 178516644, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of NaOEt (32 g, 5 eq.) in EtOH (200 mL) was slowly added compound 282 (22 g, 1 eq.). The reaction mixture was stirred at room temperature for 30 min and diethyl malonate (11.5 mL, 0.8 eq.) was then added. The suspension was refluxed for 24 hrs. The solvent was removed under reduced pressure. The residue was suspended in H2O (200 mL) and acidified to pH 5 with 2 N aqueous HCl. The resulting solid was filtered, washed with water, and dried under reduced pressure to yield compound 283 as a brown solid in 98% yield. 1H NMR (DMSO-d6, 400 MHz) δ 5.77 (s, 1H), 8.68 (s, 1H).

Workup

  1. temperatureThe suspension was refluxed for 24 hrs
  2. customThe solvent was removed under reduced pressure
  3. filtrationThe resulting solid was filtered
  4. washwashed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-8a3c7c5829324d51a0c5bd235c1aa426
Source dataset
uspto-grants-2016_05
Patent number
US09353100B2

Reaction notes

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