Methyl Isocyanate → HCID 54306683, compound
Reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[CH3:5][O:6][C:7](=[O:25])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][NH:22][OH:23])[C:16]=1[CH3:24]>O.O1CCOCC1.O>[CH3:5][O:6][C:7](=[O:25])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][N:22]([OH:23])[C:3]([NH:2][CH3:1])=[O:4])[C:16]=1[CH3:24]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Methyl isocyanate (0.33 g, 5.8 mmol) is added dropwise to 2-[[3-(N-hydroxyamino)methyl-2-methylphenyl]amino]benzoic acid methyl ester (1.5 g, 5.2 mmol) in 33% water/dioxane (60 mL) with ice bath cooling. The reaction mixture is stirred at 0° C. for 30 minutes and then at room temperature for 1 hour. It is then diluted with water (100 mL) and extracted with ethyl acetate (200 mL). The organic layer is washed with water (50 mL) and dried over magnesium sulfate. Evaporation of the ethyl acetate gives the crude product which is purified by recrystallization first from ether and then from ethyl acetate to give 2-[[3-[[hydroxy[(methylamino)carbonyl]amino]methyl]2-methylphenyl]amino]benzoic acid methyl ester (0.68 g, 38%). mp=173-175° C.
Workup
- temperaturecooling
- waitat room temperature for 1 hour
- extractionextracted with ethyl acetate (200 mL)
- washThe organic layer is washed with water (50 mL)
- dry with materialdried over magnesium sulfate
- customEvaporation of the ethyl acetate
- customgives the crude product which
- customis purified by recrystallization first from ether
Sources & evidence
- ORD record
- ord-81468cd5bacc49af95eaf918dc4bff84
- Source dataset
- uspto-grants-1991_05
- Patent number
- US05017604
Reaction notes
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