Sodium Hydroxide → HCID 58526183, compound

HRID 1184992Notes

Reaction equation

HRID 1184992 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[N:13]=[C:14]=[N:15][C:16]1[C:21]([CH:22]([CH3:24])[CH3:23])=[CH:20][CH:19]=[CH:18][C:17]=1[CH:25]([CH3:27])[CH3:26])([CH3:3])[CH3:2].[CH2:28]([N:30]([CH2:32][CH3:33])[OH:31])[CH3:29].[OH-].[Na+]>C1COCC1>[CH:22]([C:21]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:25]([CH3:27])[CH3:26])[C:16]=1[NH:15][C:14](=[N:13][C:5]1[C:6]([CH:10]([CH3:12])[CH3:11])=[CH:7][CH:8]=[CH:9][C:4]=1[CH:1]([CH3:3])[CH3:2])[O:31][N:30]([CH2:32][CH3:33])[CH2:28][CH3:29])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 19463DiethylhydroxylamineHCID 75100Bis(2,6-diisopropylphenyl)carbodiimide

Product 1

HCID 58526183HCID 58526183, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of bis(2,6-diisopropylphenyl)carbodiimide (4.35 g, 12 mmol) and N,N-diethylhydroxylamine (1.6 g, 18 mmol) in THF (20 ml) is added finely powdered NaOH (48 mg) and the mixture is stirred at room temperature for 22 hours. The reaction mixture is then filtered and the filtrate is evaporated on the rotary evaporator below 45° C. The residue is recrystallized twice from acetonitrile to afford 1.75 g of the title compound as a white solid, mp. 113-116° C.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. customthe filtrate is evaporated on the rotary evaporator below 45° C
  3. customThe residue is recrystallized twice from acetonitrile

Sources & evidence

ORD record
ord-d7c46bb4cc9b4f38b27bfeb95840abb5
Source dataset
uspto-grants-2014_03
Patent number
US08669398B2

Reaction notes

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