O-Phenylenediamine → 2-(2-(9H-fluoren-9-ylidene)acetamido)-N-(2-aminophenyl)acetamide

HRID 1926185Notes

Reaction equation

HRID 1926185 reaction equation
[CH:1]1[C:13]2[C:12](=[CH:14][C:15]([NH:17][CH2:18][C:19]([OH:21])=O)=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.C(N=C=NCCCN(C)C)C.O[C:35]1[C:43]2[N:42]=N[NH:40][C:39]=2[CH:38]=[CH:37][CH:36]=1.C(N(CC)CC)C.C1(N)C=CC=CC=1N>[Cl-].[Na+].O.CN(C=O)C>[CH:1]1[C:13]2[C:12](=[CH:14][C:15]([NH:17][CH2:18][C:19]([NH:40][C:39]3[CH:38]=[CH:37][CH:36]=[CH:35][C:43]=3[NH2:42])=[O:21])=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 7243O-PhenylenediamineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 579720622-(2-(9H-fluoren-9-ylidene)acetamido)acetic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 445402502-(2-(9H-fluoren-9-ylidene)acetamido)-N-(2-aminophenyl)acetamideYield 80%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2-(2-(9H-fluoren-9-ylidene)acetamido)acetic acid (279 mg, 1 mmol), and 8 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (394 mg, 2 mmol), hydroxy-benzotriazole (162 mg, 1.2 mmol), triethylamine (404 mg, 4 mmol) and o-phenylenediamine (432 mg, 4 mmol) were added. The mixture was stirred for 24 hours at room temperature. The mixture was diluted with 400 mL of brine. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give the title compound (295 mg, 80% yield) as a brown solid. LC-MS (m/z) 370 (M+1).

Workup

  1. additionwere added
  2. filtrationThe solids were collected by vacuum filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-67a7037ec98b4de486415a8c877e001b
Source dataset
uspto-grants-2012_05
Patent number
US08178577B2

Reaction notes

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