Sodium Sulfite → HCID 178470398, compound

HRID 2202119Notes

Reaction equation

HRID 2202119 reaction equation
Br[C:2]1[NH:3][C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([Br:7])[N:6]=1.[O-]S([O-])=O.[Na+].[Na+]>O>[Br:7][C:5]1[N:6]=[CH:2][NH:3][C:4]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

4

Reactant 2

HCID 24437Sodium SulfiteHCID 178470340HCID 178470340, compound

Product 1

HCID 178470398HCID 178470398, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of ethyl 2,4-dibromo-1H-imidazole-5-carboxylate (9 g, 30.21 mmol, 1.00 equiv) and Na2SO3 (7.2 g, 2.00 equiv) in water (80 mL) was stirred at 90° C. for 10 h. The reaction was cooled to room temperature and the solid was collected by filtration, washed with 4×20 mL of water then air-dried to afford 4.0 g (60%) of ethyl 4-bromo-1H-imidazole-5-carboxylate as a white solid. 1H-NMR (300 MHz, CD3OD): δ 7.80 (s, 1H), 4.42-4.35 (m, 2H), 1.40 (t, J=9.6 Hz, 3H) ppm. LCMS (method A, ESI): RT=1.13 min, m/z=219.0 [M+H]+.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationthe solid was collected by filtration
  3. washwashed with 4×20 mL of water
  4. customthen air-dried

Sources & evidence

ORD record
ord-4192134e9ac04d669c9ddb895e329060
Source dataset
uspto-grants-2016_06
Patent number
US09365527B2

Reaction notes

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