Sodium Hydroxide → HCID 18316284, compound

HRID 276304Notes

Reaction equation

HRID 276304 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([C:9]#[C:10][Si](C)(C)C)[CH:5]=[CH:4][C:3]=1[N:15]=[C:16]1[S:20][CH2:19][C:18]2([CH2:24][CH2:23][CH2:22][CH2:21]2)[N:17]1[CH2:25][CH:26]([CH3:28])[CH3:27].[OH-].[Na+]>CO.C(Cl)Cl>[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([C:9]#[CH:10])[CH:5]=[CH:4][C:3]=1[N:15]=[C:16]1[S:20][CH2:19][C:18]2([CH2:21][CH2:22][CH2:23][CH2:24]2)[N:17]1[CH2:25][CH:26]([CH3:28])[CH3:27]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22951382HCID 22951382, compound

Product 1

HCID 18316284HCID 18316284, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(2,3-dimethyl-4-(2-trimethylsilyl-1-ethynyl)phenylimino)-1-isobutyl-3-thia-1-azaspiro[4.4]nonane (0.005 g, 0.0125 mmol) and NaOH (0.006 g, 0.15 mmol) in MeOH (2 mL) was stirred overnight at room temp. The reaction mixture was diluted with CH2Cl2 (20 mL), filtered, and the filtrate was concentrated under reduced pressure. Thre residue was purified by preparative TLC (2% EtOAc/Hex) to give 2-(2,3-dimethyl-4-ethynylphenylimino)-1-isobutyl-3-thia-1-azaspiro[4.4]nonane (0.003.2 g, 78%): TLC (20% EtOAc/hex) Rf0.70.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThre residue was purified by preparative TLC (2% EtOAc/Hex)

Sources & evidence

ORD record
ord-675d9d2142f948a787ea07fa6907141a
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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