Ammonia → HCID 22916676, compound

HRID 1376607Notes

Reaction equation

HRID 1376607 reaction equation
[OH:1][CH2:2][C:3]1[N:4]2[CH:10]=[N:9][CH:8]=[C:5]2[S:6][CH:7]=1.[C:11](Cl)(=[O:19])OC1C=CC=CC=1.CO.[NH3:23]>N1C=CC=CC=1>[C:11]([O:1][CH2:2][C:3]1[N:4]2[CH:10]=[N:9][CH:8]=[C:5]2[S:6][CH:7]=1)(=[O:19])[NH2:23]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 15891Phenyl chloroformateHCID 15428311HCID 15428311, compound

Product 1

HCID 22916676HCID 22916676, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 0.5 g (3.24 mmol) of the 3-(hydroxymethyl)imidazo[5,1-b]thiazole prepared in Preparation 55 in 5 ml of pyridine was added 0.54 ml (4.22 mmol) of phenyl chlorocarbonate with ice-cooling, and the mixture was stirred at the temperature for 40 minutes and then at room temperature for 2.5 hours. To this solution was added with ice-cooling 20 ml of methanol saturated with ammonia, and the mixture was stirred at the temperature for 30 minutes and then at room temperature for 41 hours. The resulting mixture was concentrated under reduced pressure. The residue was purified by column chromatography using Sephadex LH 20, eluting with a 1:1 mixture of chloroform and methanol to give 0.4 g (yield 62.6%) of the title compound as light yellow crystals.

Workup

  1. temperaturecooling
  2. waitat room temperature for 2.5 hours
  3. additionTo this solution was added with ice-
  4. stirringthe mixture was stirred at the temperature for 30 minutes
  5. waitat room temperature for 41 hours
  6. concentrationThe resulting mixture was concentrated under reduced pressure
  7. customThe residue was purified by column chromatography
  8. washeluting with a 1:1 mixture of chloroform and methanol

Sources & evidence

ORD record
ord-6f50d8b9aa184842be1a69cb76af1980
Source dataset
uspto-grants-1997_09
Patent number
US05663162

Reaction notes

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