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Sodium Iodide → HCID 54003150, compound

HRID 1460727
Notes
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Reaction equation

HRID 1460727 reaction equation
[N+:1](=[C:3]([C:17]([CH3:19])=[O:18])[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)=[O:5])=[N-:2].[C:20]([Si:24](Cl)([CH3:26])[CH3:25])([CH3:23])([CH3:22])[CH3:21].[I-].[Na+].C(N(CC)CC)C>C(#N)C>[N+:1](=[C:3]([C:17]([O:18][Si:24]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:26])[CH3:25])=[CH2:19])[C:4]([O:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=1)=[O:5])=[N-:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 53872938HCID 53872938, compound

Product 1

HCID 54003150HCID 54003150, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Conditions

Temperature
40 °C

Procedure

Into 5 ml of dry acetonitrile were suspended 263 mg (1 millimole) of p-nitrobenzyl 2-diazoacetoacetate, 226 mg (1.5 millimoles) of tertbutyldimethylsilyl chloride and 210 mg (1.4 millimoles) of sodium iodide. To the mixture was added 220 μl (1.6 millimoles) of triethylamine under an argon atmosphere at a room temperature. The resultant was heated up to 40° C. and agitated at the same temperature overnight, followed by concentration under a reduced pressure. To the residue was added 20 ml of ethyl acetate, and the resultant was washed twice with 10 ml portions of water. The organic layer was dried and then concentrated to dryness under a reduced pressure to give 340 mg (yield 90%) of the desired compound in a yellow solid. The physical properties of the product were in agreement with those of the product obtained in Example 2.

Workup

  1. concentrationfollowed by concentration under a reduced pressure
  2. additionTo the residue was added 20 ml of ethyl acetate
  3. washthe resultant was washed twice with 10 ml portions of water
  4. customThe organic layer was dried
  5. concentrationconcentrated to dryness under a reduced pressure

Sources & evidence

ORD record
ord-845d709b25cb404cbdbe48a3a6b3b96a
Source dataset
uspto-grants-1991_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05071966

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes