Ammonium thiocyanate → HCID 18930395, compound

HRID 129640Notes

Reaction equation

HRID 129640 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[S-:18][C:19]#[N:20].[NH4+].BrBr>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:12][C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][C:9]=2[S:18][C:19]#[N:20])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 15666Ammonium thiocyanateHCID 24408BromineHCID 378974HCID 378974, compound

Product 1

HCID 18930395HCID 18930395, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of ethyl 5-(p-chlorophenyl)-pyrrole-2-carboxylate (0.95 g, 3.8 mmol) in acetic acid (20 mL) is treated with ammonium thiocyanate (1.75 g, 22.8 mmol), stirred at room temperature for five minutes, cooled to 15° C., treated with a solution of bromine (0.91 g, 5.7 mmol) in acetic acid (10 mL) and stirred at room temperature for several hours. The reaction mixture is filtered to remove solids and the filtrate is poured into water and stirred. The aqueous mixture is filtered to obtain an off-white solid. Flash chromatography of the solid using a 1:10 ethyl acetate/hexanes solution gives the title product as a white solid (0.99 g, mp 138°-141° C.) which is identified by 1HNMR and 13CNMR spectral analyses.

Workup

  1. temperaturecooled to 15° C.
  2. stirringstirred at room temperature for several hours
  3. filtrationThe reaction mixture is filtered
  4. customto remove solids
  5. additionthe filtrate is poured into water
  6. stirringstirred
  7. filtrationThe aqueous mixture is filtered
  8. customto obtain an off-white solid

Sources & evidence

ORD record
ord-32f94a69894e4244a10f4fce4bcd9240
Source dataset
uspto-grants-1995_11
Patent number
US05468877

Reaction notes

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