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

HRID 264021
Notes
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Reaction equation

HRID 264021 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 8857
Ethyl Acetate
Solvent

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-d44bbc50282a497da1673d545a076bb2
Source dataset
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05646172

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes