Chloroacetyl chloride → trans-2-chloro-N-(2,3,4,5-tetrahydro-5-hydroxy-7-methoxy-1-benzoxepin-4-yl)acetamide
Reaction equation
[NH2:1][C@H:2]1[C@H:8]([OH:9])[C:7]2[CH:10]=[C:11]([O:14][CH3:15])[CH:12]=[CH:13][C:6]=2[O:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[Cl:23][CH2:24][C:25](Cl)=[O:26]>C(Cl)(Cl)Cl>[Cl:23][CH2:24][C:25]([NH:1][C@H:2]1[C@H:8]([OH:9])[C:7]2[CH:10]=[C:11]([O:14][CH3:15])[CH:12]=[CH:13][C:6]=2[O:5][CH2:4][CH2:3]1)=[O:26]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 17 g of trans-4-amino-7-methoxy-2,3,4,5-tetrahydro-1-benzoxepin-5-ol dissolved in 700 ml of hydrocarbon-stabilized chloroform was treated with 16 ml of triethylamine at room temperature and 10 g of chloroacetyl chloride dissolved in 80 ml of chloroform was slowly added thereto. The reaction mixture was allowed to stand at room temperature for 24 hours and the solid removed by filtration and washed with chloroform. The filtrate was washed twice with dilute hydrochloric acid solution, followed by a wash with water and dried over anhydrous magnesium sulfate. The filtrate was evaporated to dryness and triturated with ether to yield 18.8 g of trans-2-chloro-N-(2,3,4,5-tetrahydro-5-hydroxy-7-methoxy-1-benzoxepin-4-yl)acetamide.
Workup
- additionwas slowly added
- customthe solid removed by filtration
- washwashed with chloroform
- washThe filtrate was washed twice with dilute hydrochloric acid solution
- washa wash with water
- dry with materialdried over anhydrous magnesium sulfate
- customThe filtrate was evaporated to dryness
- customtriturated with ether
Sources & evidence
- ORD record
- ord-b1eea77b75ca4e66a49e9c58bd64f7b3
- Source dataset
- uspto-grants-1988_08
- Patent number
- US04766212
Reaction notes
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