Water → HCID 15010186, compound

HRID 1651700Notes

Reaction equation

HRID 1651700 reaction equation
[Br:1][C:2]1[NH:3][CH:4]=[CH:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1.ClS([N:18]=[C:19]=O)(=O)=O.CN(C)C=O.O>C(COC)OC>[Br:1][C:2]1[NH:3][C:4]([C:19]#[N:18])=[CH:5][C:6]=1[C:7]1[CH:8]=[CH:9][C:10]([Cl:13])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 70918Chlorosulfonyl isocyanateHCID 15753019HCID 15753019, compound

Product 1

HCID 15010186HCID 15010186, compoundYield 33,151.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A freshly prepared sample of 2-bromo-3-(p-chlorophenyl)pyrrole (4.0 g., 0.015 mmol) is dissolved in dry dimethoxyethane (25 mL). Then while holding the temperature below 25° C., chlorosulfonyl isocyanate (3.08 g., 0.022 mmol) is added. After stirring overnight, the solution is treated with dimethylformamide (6 mL) and stirred for 3 hours. Finally, the solution is poured into water precipitating a brown solid (3.8 g, 90%). Dry column chromatography (80/20 hexane/ethyl acetate) yields 1.4 g (33%) of white solid with m.p. 202°-204° C.

Workup

  1. additionis added
  2. stirringstirred for 3 hours
  3. dry with materialDry column chromatography (80/20 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3e0598625b524869bd7ecc5c5fa7c3c3
Source dataset
uspto-grants-1990_05
Patent number
US04929634

Reaction notes

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