Ethanol → HCID 69947292, compound

HRID 1265285

Reaction equation

HRID 1265285 reaction equation
[C:1]([CH:9]([C:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)C)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])(=[O:22])[NH:20][NH2:21].[CH3:28]CO>CC(O)=O.O>[C:24]([O:23][C:19](=[O:22])[NH:20][N:21]1[C:12]([C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:28]=2)=[CH:11][CH:9]=[C:1]1[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([CH3:27])([CH3:26])[CH3:25]

Participants

6

Reactant 3

HCID 702EthanolHCID 70091tert-Butyl carbazateHCID 3446371,3-Diphenyl-2-methyl-1,3-propandione

Product 1

HCID 69947292HCID 69947292, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of dibenzoylethane (5 g, 21.0 mmol) and t-butyl carbazate (3.98 g, 30.1 mmol) in EtOH (170 mL) and AcOH (21 mL) was heated to reflux under Ar for 4.5 h, cooled to rt and diluted with water (400 mL). The resulting suspension was stirred under Ar at rt for 3 h, and then allowed to settle overnight at rt. The solid was filtered, washed with small portions of water and dried in vacuo to afford (2,5-Diphenyl-pyrrol-1-yl)-carbamic acid tert-butyl ester (6.72 g, 96%) as a white solid: 1H NMR (CDCl3, chemical shifts in ppm relative to TMS): 1.14 (s, 3H), 1.38 (s, 6H), 6.35 (s, 2H), 6.84 (bs, 2H), 7.29-7.53 (m, 10H).

Workup

  1. temperatureto reflux under Ar for 4.5 h
  2. waitto settle overnight at rt
  3. filtrationThe solid was filtered
  4. washwashed with small portions of water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-0c2794cb66df4629b40f1a61c306bc4c
Source dataset
uspto-grants-2003_04
Patent number
US06545108B1

Linked notes

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