1,1'-Carbonyldiimidazole → HCID 16037363, compound

HRID 657704Notes

Reaction equation

HRID 657704 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.[CH:13]([N:16]1[C:28]2[CH:27]=[C:26]([C:29]([OH:31])=O)[CH:25]=[CH:24][C:23]=2[C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2)([CH3:15])[CH3:14].C(=O)(O)O.[NH2:36][C:37]([NH2:39])=[NH:38]>CN(C=O)C>[NH2:38][C:37]([NH2:39])=[N:36][C:29]([C:26]1[CH:25]=[CH:24][C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([CH:13]([CH3:15])[CH3:14])[C:28]=2[CH:27]=1)=[O:31]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 286947Carbonic acid-guanidine (1:1)HCID 67424545HCID 67424545, compound

Product 1

HCID 16037363HCID 16037363, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A 134 mg portion of CDI was added to 4 ml DMF solution of 140 mg 9-isopropyl-9H-carbazole-2-carboxylic acid, followed by stirring at 50° C. for 1 hour. After spontaneous cooling to room temperature, 238 mg of guanidine carbonate was added thereto, followed by stirring overnight at room temperature. After evaporation of the solvent, water was added thereto and the thus precipitated solid was purified by a silica gel column chromatography (Chromatorex (registered trademark), methanol/chloroform) to obtain 157 mg of N-(diaminomethylene)-9-isopropyl-9H-carbazole-2-carboxamide as a pale yellow solid.

Workup

  1. temperatureAfter spontaneous cooling to room temperature
  2. stirringby stirring overnight at room temperature
  3. customAfter evaporation of the solvent, water
  4. additionwas added
  5. customthe thus precipitated solid was purified by a silica gel column chromatography (Chromatorex (registered trademark), methanol/chloroform)

Sources & evidence

ORD record
ord-ddd2bb61884646a1b4527ecc452f0ef2
Source dataset
uspto-grants-2011_12
Patent number
US08076348B2

Reaction notes

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