Acetic Acid → 6-Bromo-2-sulfanylidene-2,3-dihydropyrrolo[2,1-f][1,2,4]triazin-4(1H)-one

HRID 1262277Notes

Reaction equation

HRID 1262277 reaction equation
COC([C:5]1[N:6]([NH:11][C:12]([NH:14][C:15](=[O:22])C2C=CC=CC=2)=[S:13])[CH:7]=[C:8]([Br:10])[CH:9]=1)=O.[OH-].[Na+].O.C(O)(=O)C>CCOCC.C(O)C>[Br:10][C:8]1[CH:9]=[C:5]2[N:6]([CH:7]=1)[NH:11][C:12](=[S:13])[NH:14][C:15]2=[O:22]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 866616921-(3-Benzoyl-thioureido)-4-bromo-1H-pyrrole-2-carboxylic acid methyl ester

Product 1

HCID 574161296-Bromo-2-sulfanylidene-2,3-dihydropyrrolo[2,1-f][1,2,4]triazin-4(1H)-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
85 °C

Procedure

Into a 500 mL beaker, 1-(3-Benzoyl-thioureido)-4-bromo-1H-pyrrole-2-carboxylic acid methyl ester (31.20 g, 0.08162 mol) and 2.00 M of Sodium hydroxide in Water (164 mL, 0.327 mol) were added. The mixture was heated at 85° C. for 75 minutes. The reaction was cooled to RT. The solid was dissolved with Ethanol (100 mL). Acetic acid (18.8 mL, 0.332 mol) was added at 0° C. and stirred for 30 minutes. The solid was filtered and washed with cold EtOH (50 mL) to afford a white solid. The white solid was stirred in Et2O (300 mL) for 20 minutes. The solid was filtered and washed with Et2O (200 mL) to give 6-Bromo-2-thioxo-2,3-dihydro-1H-pyrrolo[2,1-f][1,2,4]triazin-4-one as a white solid. The white solid was dried under vacuum over night (11.6, 57%).

Workup

  1. temperatureThe reaction was cooled to RT
  2. filtrationThe solid was filtered
  3. washwashed with cold EtOH (50 mL)
  4. customto afford a white solid
  5. filtrationThe solid was filtered
  6. washwashed with Et2O (200 mL)

Sources & evidence

ORD record
ord-6306cb2dfed645fbb0e350e0a60843c0
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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