2-(Methylamino)acetaldehyde → 2-[1-Methyl-3-(5-bromothiazol-2-yl)ureido]acetaldehyde

HRID 1111585Notes

Reaction equation

HRID 1111585 reaction equation
[Br:1][C:2]1[S:6][C:5]([N:7]=[C:8]=[O:9])=[N:4][CH:3]=1.[CH3:10][NH:11][CH2:12][CH:13]=[O:14]>C1C=CC=CC=1>[CH3:10][N:11]([CH2:12][CH:13]=[O:14])[C:8]([NH:7][C:5]1[S:6][C:2]([Br:1])=[CH:3][N:4]=1)=[O:9]

Participants

4

Reactant 2

HCID 133161322-(Methylamino)acetaldehydeHCID 230622645-Bromothiazol-2-yl Isocyanate

Product 1

HCID 227668622-[1-Methyl-3-(5-bromothiazol-2-yl)ureido]acetaldehyde

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

5-Bromothiazol-2-yl isocyanate dimer (17.0 grams), benzene (70 ml) and the dimethyl acetal of 2-methylaminoacetaldehyde (13.5 grams) were charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The reaction mixture was then stirred at room temperature for a period of about one hour. After this time the reaction mixture was filtered, and the filtrate was stripped of solvent under reduced pressure, leaving an oil. This oil was chromatographed on silica gel using ethyl acetate as the diluant. The eluant was dissolved in an ethanol-water mixture, and the solution was filtered. The filtrate was then stripped of solvents under vacuum to yield the desired product the dimethyl acetal of 2-[1-methyl-3-(5-bromothiazol-2-yl)ureido]acetaldehyde as a crystalline solid having a melt point of 72° to 73° C.

Workup

  1. customequipped with a mechanical stirrer
  2. filtrationAfter this time the reaction mixture was filtered
  3. customleaving an oil
  4. customThis oil was chromatographed on silica gel
  5. dissolutionThe eluant was dissolved in an ethanol-water mixture
  6. filtrationthe solution was filtered

Sources & evidence

ORD record
ord-ae2ad736c79a428c805c917347f338c4
Source dataset
uspto-grants-1978_10
Patent number
US04118390

Reaction notes

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