4-Chloro-1,2-diaminobenzene → HCID 178452617, compound

HRID 2205291Notes

Reaction equation

HRID 2205291 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[C:19]([NH2:24])[CH:18]=1.[C:25]([O:29][C:30]([NH:32][C:33]1([C:38](O)=O)[CH2:37][CH2:36][O:35][CH2:34]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]>C1COCC1>[C:25]([O:29][C:30](=[O:31])[NH:32][C:33]1([C:38]2[NH:23][C:20]3[CH:21]=[CH:22][C:17]([Cl:16])=[CH:18][C:19]=3[N:24]=2)[CH2:37][CH2:36][O:35][CH2:34]1)([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 72634-Chloro-1,2-diaminobenzeneHCID 10868DicyclohexylcarbodiimideHCID 450269433-[(tert-Butoxycarbonyl)amino]oxolane-3-carboxylic acid

Product 1

HCID 178452617HCID 178452617, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N,N′-Dicyclohexylcarbodiimide (1.75 g, 8.5 mmol) is added portionwise at 0° C. to 4-chloro-o-phenylenediamine (1.21 g, 8.5 mmol) and 3-tert-Butoxycarbonylamino-tetrahydro-furan-3-carboxylic acid (1.97 g, 8.5 mmol) in THF (50 mL). After stirring overnight at rt, the reaction mixture was filtered and evaporated under reduced pressure to give a residue that is purified by flash chromatography (eluent 0-5% EtOH/DCM) to furnish [3-(5-Chloro-1H-benzoimidazol-2-yl)-tetrahydro-furan-3-yl]-carbamic acid tert-butyl ester (2.35 g, 78%).

Workup

  1. filtrationthe reaction mixture was filtered
  2. customevaporated under reduced pressure
  3. customto give a residue that
  4. customis purified by flash chromatography (eluent 0-5% EtOH/DCM)

Sources & evidence

ORD record
ord-3f2ffaa4fcfb460bb47f72d2412de11b
Source dataset
uspto-grants-2016_06
Patent number
US09371282B2

Reaction notes

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