Chloroacetyl chloride → HCID 60199172, compound
Reaction equation
[CH:1]12[C:7](=[O:8])[NH:6][CH:5]1[CH2:4][CH2:3][CH2:2]2.O1CCCC1.C(N(CC)CC)C.[Cl:21][CH2:22][C:23](Cl)=[O:24]>C(OCC)(=O)C.O>[Cl:21][CH2:22][C:23]([N:6]1[C:7](=[O:8])[CH:1]2[CH:5]1[CH2:4][CH2:3][CH2:2]2)=[O:24]Participants
Conditions
- Temperature
- 3 °C
Procedure
In a four-necked flask with a volume of 300 mL, which was equipped with a thermometer, a stirrer, a dropping funnel, and a nitrogen introducing tube, 11.1 g (100 mmol) of 6-azabicyclo[3.2.0]heptan-7-one, 100 mL of tetrahydrofuran, and 12.1 g (120 mmol) of triethylamine were charged, and an internal temperature was cooled to 3° C. 12.4 g (110 mmol) of 2-chloroacetyl chloride was added dropwise at that temperature over 15 minutes from the dropping funnel. After completion of the dropwise addition, the mixture was stirred for 3 hours. Thereafter, 50 mL of water and 50 mL of ethyl acetate were added, and a liquid separation operation was carried out. The obtained organic layer was concentrated under reduced pressure, thereby obtaining 8.4 g (45 mmol) of 6-chloroacetyl-6-azabicyclo[3.2.0]heptan-7-one having the following properties.
Workup
- additionwere charged
- additionAfter completion of the dropwise addition
- customa liquid separation operation
- concentrationThe obtained organic layer was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-a9294b2c66b14e6792eca05449d40b9f
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08859183B2
Reaction notes
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