4-Bromobutyryl chloride → N-Methyl-N-(4-bromobutyryl)acrylamide
Reaction equation
[CH3:1][N:2]([Si](C)(C)C)[C:3](=[O:6])[CH:4]=[CH2:5].[Br:11][CH2:12][CH2:13][CH2:14][C:15](Cl)=[O:16]>>[CH3:1][N:2]([C:15](=[O:16])[CH2:14][CH2:13][CH2:12][Br:11])[C:3](=[O:6])[CH:4]=[CH2:5]Participants
Procedure
In a nitrogen glove bag 7.27 g (0.05 mole) of N-methyl-N-trimethylsilylacrylamide was placed in a one-necked flask. The flask was fitted with an additional funnel topped with a drying tube. With the flask contents cooled to ice/water temperatures, 9.28 g (0.05 mole) of 4-bromobutyryl chloride was added dropwise through a dropping funnel to the flask over a period of half an hour. The resulting yellow clear mixture was stirred for an additional two hours. The disappearance of the acyl chloride carbonyl band (1800 cm-1) and the increase in intensity of the product amide band (1670 cm-1) was monitored by IR. The by-product trimethylsilyl chloride was removed in vacuo to give 13 g of product. It was used in the next step without further purification.
Workup
- customThe flask was fitted with an additional funnel
- customtopped with a drying tube
- additionwas added dropwise through a dropping funnel to the flask over a period of half an hour
- customThe by-product trimethylsilyl chloride was removed in vacuo
Sources & evidence
- ORD record
- ord-3ea2192fe57042aba4126e24d7156033
- Source dataset
- uspto-grants-1996_10
- Patent number
- US05560749
Reaction notes
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