Hydrochloric Acid → HCID 13752454, compound

HRID 1905590Notes

Reaction equation

HRID 1905590 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]([C:12]2[NH:13][C:14](=[O:21])[C:15]([CH:18]([CH3:20])[CH3:19])([CH3:17])[N:16]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C[O-].[Na+].Cl[CH:26]([F:28])[F:27].Cl>CO>[F:27][CH:26]([F:28])[O:1][C:2]1[CH:3]=[N:4][C:5]([C:12]2[NH:13][C:14](=[O:21])[C:15]([CH:18]([CH3:19])[CH3:20])([CH3:17])[N:16]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6372ChlorodifluoromethaneHCID 10942334Sodium MethoxideHCID 135745182HCID 135745182, compound

Product 1

HCID 13752454HCID 13752454, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

Into a solution containing 1.25 g methyl 5-hydroxy-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinate and 1.40 g sodium methoxide in 50 mL absolute methanol at 50° C. is passed through a dispersion tube, chlorodifluoromethane for one hour. The mixture is cooled to 5° C. and the pH adjusted to 5 with 2N methanolic HCl. The solution is filtered and the filtrate concentrated in vacuo. The residue is extracted with 2×100 mL ether, the extracts combined, dried and concentrated. The residue is chromatographed on silica gel using ether as the eluant to give the product, analytically pure methyl 5-difluoromethoxy-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinate as a white crystalline solid, mp 104°-105° C.

Workup

  1. customis passed through a dispersion tube
  2. filtrationThe solution is filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. extractionThe residue is extracted with 2×100 mL ether
  5. customdried
  6. concentrationconcentrated
  7. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-49b3a868b8ab485eafd29110e57d7981
Source dataset
uspto-grants-1987_03
Patent number
US04647301

Reaction notes

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