Nitrogen → 5-Chloromethyl-2-(2-methyl-[1,3]dioxolan-2-yl)-thiazole
Reaction equation
N#N.[CH3:3][C:4]1([C:9]2[S:10][C:11]([CH2:14]O)=[CH:12][N:13]=2)[O:8][CH2:7][CH2:6][O:5]1.CCN(CC)CC.S([Cl:27])(C)(=O)=O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:27][CH2:14][C:11]1[S:10][C:9]([C:4]2([CH3:3])[O:8][CH2:7][CH2:6][O:5]2)=[N:13][CH:12]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [2-(2-methyl-[1,3]dioxolan-2-yl)-thiazol-5-yl]-methanol (560 mg, 2.78 mmol) in dry CH2Cl2 (5.0 mL) was treated at 0° C. with Et3N (0.50 mL, 3.60 mmol) followed by DMAP (34 mg, 0.28 mmol) and Ms-Cl (0.28 mL, 3.51 mmol). After stirring at 0° C. for 1 h, the reaction mixture was quenched with water (10 mL), extracted with CH2Cl2 (10 mL) and the combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (5:1 to 2:1 hept-EA) gave the title compound as a pale yellow oil. TLC:rf (1:2 hept-EA)=0.50. LC-MS-conditions 01: tR=0.81 min; [M+H]+=219.89.
Workup
- customthe reaction mixture was quenched with water (10 mL)
- extractionextracted with CH2Cl2 (10 mL)
- dry with materialextracts were dried over Na2SO4
- filtrationfiltered
- customthe solvents were removed under reduced pressure
- customPurification of the residue by FC (5:1 to 2:1 hept-EA)
Sources & evidence
- ORD record
- ord-b9f945bf85c649afb0e80444b41a5a57
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08536209B2
Reaction notes
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