1-Chloroethyl chloroformate → HCID 68429606, compound
Reaction equation
C([N:8]1[CH2:14][C:13]2[CH:15]=[CH:16][C:17]([S:19][CH:20]([CH3:22])[CH3:21])=[N:18][C:12]=2[O:11][CH2:10][CH2:9]1)C1C=CC=CC=1.[Cl:23]C(OC(Cl)C)=O>ClC(Cl)C>[ClH:23].[CH:20]([S:19][C:17]1[CH:16]=[CH:15][C:13]2[CH2:14][NH:8][CH2:9][CH2:10][O:11][C:12]=2[N:18]=1)([CH3:22])[CH3:21]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a solution of the compound obtained in step 2 (0.24 g) in dichloroethane (5 mL) was added 1-chloroethyl chloroformate (0.090 mL), and the resulting mixture was stirred at 90° C. for 2 hr. The solvent was evaporated under reduced pressure, and methanol (5 mL) was added. The mixture was stirred at 80° C. for 2 hr. The solvent was evaporated under reduced pressure, the residue was crystallized from ethanol-diisopropyl ether, and the obtained solid was purified by preparative HPLC. To the obtained residue was added 4N hydrogen chloride/ethyl acetate, and the resulting mixture was recrystallized from ethanol-diisopropyl ether to give the title compound (0.11 g, 56%) as a white powder.
Workup
- customThe solvent was evaporated under reduced pressure, and methanol (5 mL)
- additionwas added
- stirringThe mixture was stirred at 80° C. for 2 hr
- customThe solvent was evaporated under reduced pressure
- customthe residue was crystallized from ethanol-diisopropyl ether
- customthe obtained solid was purified by preparative HPLC
- additionTo the obtained residue was added 4N hydrogen chloride/ethyl acetate
- customthe resulting mixture was recrystallized from ethanol-diisopropyl ether
Sources & evidence
- ORD record
- ord-3a2f613df41b4acdba4f5035db9f4619
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08329687B2
Reaction notes
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