Hydrogen Bromide → HCID 68902424, compound

HRID 1436417Notes

Reaction equation

HRID 1436417 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH2:11][S:12][C:13]#[N:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].[BrH:16].[OH-].[Na+].O>C(O)(=O)C>[Br:16][C:13]1[S:12][CH:11]=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[N:14]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 962WaterHCID 14798Sodium HydroxideHCID 19884882-(4-Nitrophenyl)-2-oxoethyl thiocyanate

Product 1

HCID 68902424HCID 68902424, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-(4-Nitrophenyl)-2-oxoethyl thiocyanate (3.0 g; 15.4 mmol) and 50 mL of 30% HBr in acetic acid were stirred at room temperature under nitrogen overnight. The yellow paste was neutralized with 60 mL of 2N NaOH and 60 mL of H2O. The residue was collected by suction filtration. Purification of the residue on silica gel using a stepwise gradient of 5-50% ethyl acetate:hexane gave 2-bromo-4-(4-nitrophenyl)-1,3-thiazole (2.0 g, 45%), MS (ES) m/z 286[M+H]+.

Workup

  1. filtrationThe residue was collected by suction filtration
  2. customPurification of the residue on silica gel using a stepwise gradient of 5-50% ethyl acetate

Sources & evidence

ORD record
ord-035e9b0379814ac0b00bc3e4b82f5040
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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