Dimethylformamide → HCID 20084709, compound

HRID 2226266Notes

Reaction equation

ClS([N:5]=C=O)(=O)=O.[Br:8][C:9]1[N:10]([O:25][CH3:26])[C:11]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[C:12]([Br:17])[C:13]=1[C:14](O)=O.CN(C)C=O>O.C(Cl)Cl.C(OCC)(=O)C>[Br:8][C:9]1[N:10]([O:25][CH3:26])[C:11]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[C:12]([Br:17])[C:13]=1[C:14]#[N:5]

Participants

Conditions

Temperature: 5 °C

Procedure

Chlorosulfonyl isocyanate (1.66 g, 0.0117 mol) is added to a 5° C. stirred solution of 2,4-dibromo-5-(p-chlorophenyl)-1-methoxypyrrole-3-carboxylic acid (2.0 g, 0.0049 mol) in acetronitrile. The solution is heated to 45°-50° C. for 2 hours, acetronitrile is added, cooled to 5° C. and dimethylformamide (1.9 mL, 0.0244 mol) is added. The reaction mixture is stirred at room temperature for 3 hours, diluted with water and extracted with chloroform. The combined chloroform extracts are washed sequentially with water and saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate and concentrated in vacuo to give a yellow solid. Chromatography using silica gel, methylene chloride and 3% ethyl acetate in methylene chloride as eluent yields the title compound as an off-white solid (0.23 g, 12%), mp 195°-197° C.

Workup

temperatureThe solution is heated to 45°-50° C. for 2 hours
additionacetronitrile is added
extractionextracted with chloroform
washThe combined chloroform extracts are washed sequentially with water and saturated sodium bicarbonate solution
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo
customto give a yellow solid

Sources & evidence

ORD record: ord-cf4dd6ede5e642108f2b6641b7c8e784
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05347016

Reaction notes

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