Methyl Isocyanate → HCID 54358359, compound
Reaction equation
[C:1]([S:20][C@@H:21]1[O:29][C@H:28]([CH2:30][OH:31])[C@@H:26]([OH:27])[C@H:24]([OH:25])[C@H:22]1[OH:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:32][N:33]=[C:34]=[O:35]>CN(C)C=O>[C:1]([S:20][C@@H:21]1[O:29][C@H:28]([CH2:30][O:31][C:34](=[O:35])[NH:33][CH3:32])[C@@H:26]([O:27][C:34](=[O:35])[NH:33][CH3:32])[C@H:24]([O:25][C:34](=[O:35])[NH:33][CH3:32])[C@H:22]1[O:23][C:34](=[O:35])[NH:33][CH3:32])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
S-Trityl-1-thio-β-D-glucopyranose (0.70 g., 1.6 mmole) is dissolved in 20 ml. of dry dimethylformamide. Methyl isocyanate (1.5 ml.) is added and the mixture is stirred for 1.5 hours at room temperature and for an additional two hours at 65° C. The solvent is evaporated at reduced pressure, the residue is triturated with water and neutralized to pH 4 with dilute hydrochloric acid. Extracting the organic materials into chloroform, evaporating the chloroform extract and chromatographing the residue on a silica column with ethyl acetate eluant gives S-trityl-2,3,4,6-tetra-O-(N-methylcarbamoyl)-1-thio-β-D-glucopyranose.
Workup
- customThe solvent is evaporated at reduced pressure
- customthe residue is triturated with water and neutralized to pH 4 with dilute hydrochloric acid
- extractionExtracting the organic materials into chloroform
- customevaporating the chloroform
- extractionextract
Sources & evidence
- ORD record
- ord-0386638d4cf24bcb8f7d1521dc3432af
- Source dataset
- uspto-grants-1978_06
- Patent number
- US04096249
Reaction notes
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