O-Phenylenediamine → HCID 58817290, compound
Reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:19]1([NH2:26])[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH2:25].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:14](=[O:16])[NH:25][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[NH2:26])=[CH:17][CH:18]=1)([CH3:2])([CH3:3])[CH3:4]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of 4-((t-butoxycarbonylamino)methyl)benzoic acid (6.08 g, 24.2 mmol) in DMF was added o-phenylene diamine (2.9 g, 29 mmol), EDCI (9.3 g, 48.4 mmol) and HOBt (3.8 g, 24.2 mmol). TEA (11.8 mL, 84.8 mmol) was added drop wise with constant stirring to the above reaction mixture, which was stirred at room temperature overnight. Subsequently, the reaction mixture was evaporated to half its volume; the resulting solution was dissolved in ethyl acetate, washed successively with saturated NaHCO3 (3×50 mL) and brine solution (3×50 mL). The organic layer was dried over Na2SO4 and concentrated to give the pure compound (4.6 g, 56% yield).
Workup
- stirringwas stirred at room temperature overnight
- customSubsequently, the reaction mixture was evaporated to half its volume
- dissolutionthe resulting solution was dissolved in ethyl acetate
- washwashed successively with saturated NaHCO3 (3×50 mL) and brine solution (3×50 mL)
- dry with materialThe organic layer was dried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-5c80b4aef3ce467c89cbcaf239496e9d
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08476255B2
Reaction notes
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