Cesium carbonate → HCID 68712104, compound

HRID 1818828Notes

Reaction equation

HRID 1818828 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[NH:11][S:10]1(=[O:19])=[O:18].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:26][CH2:27]/[CH:28]=[CH:29]\[CH2:30]Cl>CN(C)C=O.C(OCC)C>[Cl:26][CH2:27]/[CH:28]=[CH:29]\[CH2:30][N:11]1[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:9]([C:3]2[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[F:1])[S:10]1(=[O:19])=[O:18]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 64321151,4-Dichloro-cis-2-buteneHCID 68708401HCID 68708401, compound

Product 1

HCID 68712104HCID 68712104, compoundYield 75.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
22 °C

Procedure

A solution of -(2-fluoro-4-methylphenyl)-1,3-dihydro-2,1,3-benzothiadiazole2,2-dioxide (0.5 g, 1.8 mmol) in dimethylformamide (15 mL) was treated with cesium carbonate (1.2 g, 3 mmol) and cis-1,4-dichloro-2-butene (3.2 mL, 20 mmol) and stirred at 22° C. for 14 h. The reaction mixture was diluted with ethyl ether (100 mL), washed with 2 M hydrochloric acid (100 mL) and concentrated. Flash chromatography (SiO2, 10→50% ethyl acetate/hexanes) provided 1-[(2Z)-4-chlorobut-2-en-1-yl]-3-(2-fluoro-4-methylphenyl)-1,3-dihydro-2,1,3-benzothiadiazole2,2-dioxide (0.5 g) as a yellow oil:

Workup

  1. washwashed with 2 M hydrochloric acid (100 mL)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-ce955e40c84b4724ac553d16c4593478
Source dataset
uspto-grants-2009_10
Patent number
US07601722B2

Reaction notes

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