Water → 1-Iodo-2-cyano-4-propoxy-benzene
Reaction equation
O=S(Cl)Cl.[I:5][C:6]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH3:18])=[CH:11][C:7]=1[C:8]([NH2:10])=O.O>CN(C=O)C>[I:5][C:6]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH3:18])=[CH:11][C:7]=1[C:8]#[N:10]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 115 °C
Procedure
1.67 mL (22.9 mmol) SOCl2 are added to 1.40 g (4.59 mmol) 2-iodo-5-propoxy-benzamide (XXIX.1) in 40 mL DMF. The mixture is stirred at 115° C. for 1 h. After that time, water is added and the mixture is extracted with EtOAc (3×). The combined organic layers are washed with water and brine, dried over sodium sulphate and the solvent is removed in vacuo. The crude product is purified by column chromatography (silica gel, heptane/EtOAc 100/0→60/40).
Workup
- extractionthe mixture is extracted with EtOAc (3×)
- washThe combined organic layers are washed with water and brine
- dry with materialdried over sodium sulphate
- customthe solvent is removed in vacuo
- customThe crude product is purified by column chromatography (silica gel, heptane/EtOAc 100/0→60/40)
Sources & evidence
- ORD record
- ord-a0b5b6a789ff4f9f948b06fda70b774f
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08877754B2
Reaction notes
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