Water → HCID 15010190, compound

HRID 1085615Notes

Reaction equation

HRID 1085615 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][CH:10]=[CH:11][C:12]=2[C:13]#[N:14])=[CH:4][CH:3]=1.ClS([N:19]=[C:20]=O)(=O)=O.CN(C)C=O.O>C(COC)OC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:9][C:10]([C:20]#[N:19])=[CH:11][C:12]=2[C:13]#[N:14])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 70918Chlorosulfonyl isocyanateHCID 146232102-(4-Chlorophenyl)-1H-pyrrole-3-carbonitrile

Product 1

HCID 15010190HCID 15010190, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A sample of 2-p-chlorophenyl-3-cyanopyrrole, prepared by the method of Example 4, (3.0 g, 0.015 mole) is dissolved in 50 mL of dry dimethoxyethane. To this solution is added chlorosulfonyl isocyanate (3.39 g, 0.024 mole). The addition is exothermic and some cooling is necessary. After stirring 3 hours at room temperature, dimethylformamide (6-7 mL) is added and the solution is stirred 4 hours more. The solution is then poured into water precipitating a white solid (3.4 g, 100%). A sample (1.0 g) is purified by dissolving in ethyl acetate and then passing the solution through a 60 mL course filter funnel packed with silica gel. The filtrate is concentrated to yield 0.7 g of a white solid with m.p. 235°-240° C.

Workup

  1. additionThe addition
  2. stirringthe solution is stirred 4 hours more
  3. customA sample (1.0 g) is purified
  4. dissolutionby dissolving in ethyl acetate
  5. filtrationfilter funnel
  6. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-c607f5c36f58457ebb4b13e03b87c590
Source dataset
uspto-grants-1991_04
Patent number
US05010098

Reaction notes

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