Dichloromethane → HCID 82004536, compound

HRID 2042805Notes

Reaction equation

HRID 2042805 reaction equation
[H-].[Na+].[F:3][CH:4]([F:7])[CH2:5][OH:6].C(Cl)Cl.Cl[C:12]1[N:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=[O:15]>O.C1COCC1>[Cl:21][C:19]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[C:12]([O:6][CH2:5][CH:4]([F:7])[F:3])[N:20]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 1361872,2-Difluoroethan-1-olHCID 8540472,6-Dichloronicotinic acid

Product 1

HCID 82004536HCID 82004536, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

NaH (55% dispersion in oil; 5.0 g, 114.6 mmol) is added portionwise at 10° C. to 2,2-difluoroethanol (6.25 mL, 99.0 mmol), DCM (200 mL) and THF (75 mL). After 10 min 2,6-dichloro-nicotinic acid (5.0 g, 24.7 mmol) is added to the reaction mixture and it is stirred at rt overnight. Then water is added and it is concentrated. The residue is diluted with water and extracted with Et2O. Formic acid is added to the aqueous layers the precipitate is filtered off, washed with water and dried to give the sub-title compound.

Workup

  1. concentrationit is concentrated
  2. additionThe residue is diluted with water
  3. extractionextracted with Et2O
  4. additionFormic acid is added to the aqueous layers the precipitate
  5. filtrationis filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-3f92e20ce98a4fbfa134fc2bc4e3256f
Source dataset
uspto-grants-2013_11
Patent number
US08586604B2

Reaction notes

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