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Oxalic Acid → N-(t-butoxycarbonylmethyl)carbazole

HRID 2056234
Notes
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Reaction equation

HRID 2056234 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Br[CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C(O[K])(C)(C)C.C(O)(=O)C(O)=O>CN(C)C=O>[C:19]([O:18][C:16]([CH2:15][N:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)=[O:17])([CH3:22])([CH3:21])[CH3:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 6854CarbazoleHCID 79177tert-Butyl bromoacetateHCID 178418922HCID 178418922, compound

Product 1

HCID 12010462N-(t-butoxycarbonylmethyl)carbazoleYield 46.9%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

100 g of carbazole, 117 g of t-butyl bromoacetate, and 67 g of t-butoxy potassium were dissolved in 1,000 g of dimethylformamide. The mixture was reacted overnight at room temperature. After the addition of 300 g of 5 wt % oxalic acid aqueous solution, the reaction mixture was extracted with 2,000 g of n-hexane. Precipitate obtained by crystallization in a mixed solvent of 500 g of dimethylformamide and 500 g of n-hexane was dried under vacuum to obtain 79 g of N-(t-butoxycarbonylmethyl)carbazole as a white solid. This compound is indicated as “other dye (D-2)”.

Workup

  1. customThe mixture was reacted overnight at room temperature
  2. extractionthe reaction mixture was extracted with 2,000 g of n-hexane
  3. customPrecipitate obtained by crystallization in a mixed solvent of 500 g of dimethylformamide and 500 g of n-hexane
  4. customwas dried under vacuum

Sources & evidence

ORD record
ord-7f104f62546646658c37a01fac398803
Source dataset
uspto-grants-2008_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07335457B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes