Ammonium Chloride → HCID 86698167, compound

HRID 623878Notes

Reaction equation

HRID 623878 reaction equation
C(Cl)(=O)C(Cl)=O.[OH:7][CH2:8][C:9]1[N:10]=[CH:11][C:12]([C:15]2[CH:29]=[CH:28][C:18]([O:19][CH2:20][C:21]([CH3:27])([CH3:26])[C:22]([O:24][CH3:25])=[O:23])=[CH:17][CH:16]=2)=[N:13][CH:14]=1.[Cl-].[NH4+]>C(OCC)(=O)C.C(N(CC)CC)C.C(Cl)Cl.CS(C)=O>[CH:8]([C:9]1[N:10]=[CH:11][C:12]([C:15]2[CH:29]=[CH:28][C:18]([O:19][CH2:20][C:21]([CH3:27])([CH3:26])[C:22]([O:24][CH3:25])=[O:23])=[CH:17][CH:16]=2)=[N:13][CH:14]=1)=[O:7]

Participants

8

Reactant 3

HCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 67973293HCID 67973293, compound

Product 1

HCID 86698167HCID 86698167, compoundYield 89.9%

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a methylene chloride (11 mL) solution of oxalyl chloride (355 μL) was added dropwise a methylene chloride (2 mL) solution of dimethylsulfoxide (450 μL) at −78° C., and the mixture was stirred for 15 minutes. To the mixture was added dropwise a methylene chloride (6 mL) solution of methyl 3-{4-[5-(hydroxymethyl)pyrazin-2-yl]-phenoxy}-2,2-dimethylpropanoate (655 mg) at −78° C., and the mixture was stirred for 10 minutes, and the mixture was stirred for 1 hour and 30 minutes. Triethylamine (2.05 mL) was added to the mixture, the temperature of the mixture was raised to 0° C., and the mixture was stirred for 30 minutes. To the reaction mixture were added a saturated aqueous ammonium chloride solution and ethyl acetate, and the organic layer was separated. The aqueous layer was extracted twice with ethyl acetate. The organic layers were combined, washed twice with water, and with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=95:5 to 75:25) to obtain methyl 3-{4-[5-formylpyrazin-2-yl]phenoxy}-2,2-dimethylpropanoate (585 mg).

Workup

  1. stirringthe mixture was stirred for 10 minutes
  2. stirringthe mixture was stirred for 1 hour and 30 minutes
  3. stirringthe mixture was stirred for 30 minutes
  4. customthe organic layer was separated
  5. extractionThe aqueous layer was extracted twice with ethyl acetate
  6. washwashed twice with water
  7. dry with materialwith saturated brine, dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=95:5 to 75:25)

Sources & evidence

ORD record
ord-81ab4f9bcde74e66a1343f9f632c08a9
Source dataset
uspto-grants-2016_04
Patent number
US09302996B2

Reaction notes

Loading…