4-Chloro-1,2-diaminobenzene → HCID 178477901, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.[CH2:10]([N:17]1[CH2:22][CH2:21][O:20][CH:19]([C:23](O)=O)[CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[Na+]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:23]([CH:19]3[O:20][CH2:21][CH2:22][N:17]([CH2:10][C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH2:18]3)=[N:9][C:4]=2[CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
A mixture of 4-chlorobenzene-1,2-diamine (2.0 g, 14.03 mmol) and 4-benzylmorpholine-2-carboxylic acid (4.66 g, 21.04 mmol) in polyphosphoric acid (20 mL) was stirred at 140° C. overnight. The reaction mixture was cooled to room temperature and treated with 100 mL of water. The aqueous phase was adjusted to weakly basic with 2 N aqueous sodium hydroxide and extracted with EtOAc. The organic phase was dried over MgSO4 and concentrated in vacuo to give the crude product as a off-white solid. The residue was triturated with hex/EtOAc (1×25 mL). The resulting solid was filtered, rinsed with n-hexane, and collected. The solvent was evaporated in vacuo to afford the title compound (2.1 g). LC-MS (ES) m/z=328 [M+H]+.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- extractionextracted with EtOAc
- dry with materialThe organic phase was dried over MgSO4
- concentrationconcentrated in vacuo
- customto give the crude product as a off-white solid
- customThe residue was triturated with hex/EtOAc (1×25 mL)
- filtrationThe resulting solid was filtered
- washrinsed with n-hexane
- customcollected
- customThe solvent was evaporated in vacuo
Sources & evidence
- ORD record
- ord-c017cfd3abec42b8ac8203f28a2d4bda
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08697685B2
Reaction notes
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