N-bromobutanimide → HCID 67251793, compound

HRID 2427267Notes

Reaction equation

HRID 2427267 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][S:9][C:10]=1[CH3:11])=[O:5])[CH3:2].[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.[W]>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][S:9][C:10]=1[CH2:11][Br:12])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 12300671Ethyl 5-methylthiazole-4-carboxylate

Product 1

HCID 67251793HCID 67251793, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 23964TungstenCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Heat to reflux a mixture of 5-methyl-thiazole-4-carboxylic acid ethyl ester (4.87 g, 28.5 mmol) and N-bromosuccinimide (5.06 g, 28.5 mmol) in CCl4 (100 mL) by irradiation with a 275 watt tungsten sun lamp. After 3 h, cool to room temperature and filter off a tan solid. Concentrate the filtrate by rotavap to give 6.42 g crude product as an orange oil. Purify on silica gel [115 g, 0-15% (2M NH3/MeOH)/(1:1 CH2Cl2/hexanes)] to give 3.61 g (51%) of the title compound as a yellow solid. LC-ES/MS m/z 250, 252 (M+1), TR=2.0 min (86%). Starting material: m/z 172 (M+1), TR=1.7 min (14%).

Workup

  1. temperatureHeat
  2. temperatureto reflux
  3. filtrationfilter off a tan solid
  4. concentrationConcentrate the filtrate by rotavap
  5. customto give 6.42 g crude product as an orange oil
  6. customPurify on silica gel [115 g, 0-15% (2M NH3/MeOH)/(1:1 CH2Cl2/hexanes)]

Sources & evidence

ORD record
ord-4f96c8b9ead14470b73b6f148d9436c2
Source dataset
uspto-grants-2011_06
Patent number
US07968587B2

Reaction notes

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