Methanol → 4-(2,4-Dioxo-8-methyl-1,3,8-triazaspiro[4.5]-decan-3-yl)-2-(trifluoromethyl)-benzonitrile

HRID 725218Notes

Reaction equation

HRID 725218 reaction equation
N=[C:2]1[C:6]2([CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]2)[NH:5][C:4](=[O:13])[N:3]1[C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[C:16]([C:22]([F:25])([F:24])[F:23])[CH:15]=1.C[OH:27].[OH-].[NH4+].[Cl-].[Na+]>C(OCC)(=O)C>[O:13]=[C:4]1[N:3]([C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[C:16]([C:22]([F:25])([F:24])[F:23])[CH:15]=2)[C:2](=[O:27])[C:6]2([CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]2)[NH:5]1

Participants

6

Reactant 4

HCID 887MethanolHCID 5234Sodium ChlorideHCID 14923Ammonium HydroxideHCID 21846478HCID 21846478, compound

Product 1

HCID 218464874-(2,4-Dioxo-8-methyl-1,3,8-triazaspiro[4.5]-decan-3-yl)-2-(trifluoromethyl)-benzonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Using the procedure of Example 2, 3 g of the product of Example 22, 70 ml of methanol and 17 ml of 2N hydrochloric were reacted and the solution was refluxed for 90 minutes. It was poured into 200 ml of ammonium hydroxide+100 g of ice saturated with sodium chloride and extraction was carried out 4 times with ethyl acetate. The extracts were washed with salt water, dried and purified on silica with methylene chloride-methanol: 9-1 as eluant. After crystallization from methylene chloride-isopropyl ether, 2.12 g of the expected product (white crystals) melting at 188°-189° C. were obtained.

Workup

  1. customhydrochloric were reacted
  2. temperaturethe solution was refluxed for 90 minutes
  3. washThe extracts were washed with salt water
  4. customdried
  5. custompurified on silica with methylene chloride-methanol
  6. customAfter crystallization from methylene chloride-isopropyl ether

Sources & evidence

ORD record
ord-46beca51e86d4bf592c55a56f8a03990
Source dataset
uspto-grants-1998_01
Patent number
US05705654

Reaction notes

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