Water → HCID 69592328, compound

HRID 325045Notes

Reaction equation

HRID 325045 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](Cl)(=[O:10])=[O:9].N[C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([O:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=2)[CH:14]=1.O.CCOC(C)=O.[N:38]1C=CC=CC=1>>[C:29]([C:26]1[CH:25]=[CH:24][C:23]([CH2:22][CH2:21][O:20][C:15]2[CH:14]=[C:13]([C:7]3[C:2]([Cl:1])=[C:3]([S:8]([NH2:38])(=[O:10])=[O:9])[CH:4]=[CH:5][CH:6]=3)[CH:18]=[C:17]([CH3:19])[CH:16]=2)=[CH:28][CH:27]=1)#[N:30]

Participants

6

Reactant 5

HCID 962WaterHCID 1049PyridineHCID 8857Ethyl AcetateHCID 761872-Chlorobenzenesulfonyl chlorideHCID 22033482HCID 22033482, compound

Product 1

HCID 69592328HCID 69592328, compoundYield 78%

Procedure

2-Chlorophenylsulfonyl chloride (0.152 g; 0.72 mmol) was added to a cooled solution (ice:water temperature) of amino-3-[2-(4-cyanophenyl)ethoxy]-5-methylbenzene (0.16 g; 0.60 mmol; from Example 17(iii) above) in pyridine (5 mL), and the resultant orange solution was stirred for 4 hours. Addition of H2O (30 mL), extraction with EtOAc, drying (MgSO4), evaporation of the solvent, and purification by flash chromatography (SiO2; 25-33% EtOAc:hexane) yielded 0.20 g (78%) of the sub-title compound.

Workup

  1. customdrying
  2. custom(MgSO4), evaporation of the solvent, and purification by flash chromatography (SiO2; 25-33% EtOAc:hexane)

Sources & evidence

ORD record
ord-e072756cf4ff493bb7a971d2b5e3791f
Source dataset
uspto-grants-2001_04
Patent number
US06221898B1

Reaction notes

Loading…