Bis(2,6-diisopropylphenyl)carbodiimide → HCID 58526173, compound

HRID 1184988Notes

Reaction equation

HRID 1184988 reaction equation
[C:1]([O:4][CH:5]1[CH2:10][C:9]([CH3:12])([CH3:11])[N:8]([OH:13])[C:7]([CH3:15])([CH3:14])[CH2:6]1)(=[O:3])[CH3:2].[CH:16]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]([CH3:27])[CH3:26])[C:20]=1[N:28]=[C:29]=[N:30][C:31]1[C:36]([CH:37]([CH3:39])[CH3:38])=[CH:35][CH:34]=[CH:33][C:32]=1[CH:40]([CH3:42])[CH3:41])([CH3:18])[CH3:17]>O1CCCC1>[CH:40]([C:32]1[CH:33]=[CH:34][CH:35]=[C:36]([CH:37]([CH3:39])[CH3:38])[C:31]=1[NH:30][C:29]([O:13][N:8]1[C:9]([CH3:12])([CH3:11])[CH2:10][CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:6][C:7]1([CH3:15])[CH3:14])=[N:28][C:20]1[C:19]([CH:16]([CH3:18])[CH3:17])=[CH:24][CH:23]=[CH:22][C:21]=1[CH:25]([CH3:27])[CH3:26])([CH3:42])[CH3:41]

Participants

4

Reactant 2

HCID 75100Bis(2,6-diisopropylphenyl)carbodiimideHCID 587880HCID 587880, compound

Product 1

HCID 58526173HCID 58526173, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
52 °C

Procedure

To a solution of 4-acetoxy-1-hydroxy-2,2,6,6-tetramethylpiperidine (2.63 g, 12.2 mmol, [prepared as described in Example 1] in tetrahydrofuran (10 ml) is added bis(2,6-diisopropylphenyl)carbodiimide (4.52 g, 12.5 mmol) and the solution is heated to 52° C. under argon for 20 hours. The reaction mixture is evaporated and the residue chromatographed on silica gel with hexane-ethylacetate (5:1). The pure fractions are recrystallized from hexane to afford 1.87 g of the compound 10 as colorless crystals, mp. 144-147° C.

Workup

  1. customThe reaction mixture is evaporated
  2. customthe residue chromatographed on silica gel with hexane-ethylacetate (5:1)
  3. customThe pure fractions are recrystallized from hexane

Sources & evidence

ORD record
ord-91cf5e8d162a428e9573715703b688dc
Source dataset
uspto-grants-2014_03
Patent number
US08669398B2

Reaction notes

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