Chloroacetic Acid → 2-Chloro-N-(4-methoxyphenyl)acetamide
Reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[Cl:10][CH2:11][C:12](O)=[O:13].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl>[Cl:10][CH2:11][C:12]([NH:7][C:6]1[CH:8]=[CH:9][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:13]Participants
7
Conditions
- Temperature
- 30 °C
Procedure
A mixture of 4-methoxyaniline (5.00 g, 40.6 mmol), chloroacetic acid (8.6 g, 91.5 mmol), EDCI (12.0 g, 61.2 mmol), HOBT (8.4 g, 61.3 mmol) and NMM (13 mL, 122 mmol) in anhydrous CH2Cl2 (50 mL) was stirred at 30° C. for 3 hours. The mixture was quenched with ice water, and then extracted with CH2Cl2 (30 mL×2). The combined organic layers were washed with brine (30 mL), dried over Na2SO4, filtered and concentrated to give the crude product, which was purified by silica gel column (PE/EtOAc=5/1) to give the product (1.60 g, yield 20%).
Workup
- customThe mixture was quenched with ice water
- extractionextracted with CH2Cl2 (30 mL×2)
- washThe combined organic layers were washed with brine (30 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customto give the crude product, which
- customwas purified by silica gel column (PE/EtOAc=5/1)
Sources & evidence
- ORD record
- ord-e470cd348af6462c9a38f6e61fb648c5
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09139528B2
Reaction notes
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