Benzene → 2-[1-Chloromethyl-3-(5-bromothiazol-2-yl)ureido]acetaldehyde

HRID 1764463Notes

Reaction equation

HRID 1764463 reaction equation
[Br:1][C:2]1[S:6][C:5]([N:7]=[C:8]=[O:9])=[N:4][CH:3]=1.C1C=CC=CC=1.[Cl:16][CH2:17][NH:18][CH2:19][CH:20]=[O:21]>C(O)C.O>[Cl:16][CH2:17][N:18]([CH2:19][CH:20]=[O:21])[C:8]([NH:7][C:5]1[S:6][C:2]([Br:1])=[CH:3][N:4]=1)=[O:9]

Participants

5

Reactant 3

HCID 241BenzeneHCID 203927162-ChloromethylaminoacetaldehydeHCID 230622645-Bromothiazol-2-yl Isocyanate

Product 1

HCID 227684992-[1-Chloromethyl-3-(5-bromothiazol-2-yl)ureido]acetaldehyde

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

5-Bromothiazol-2-yl isocyanate dimer (17.0 grams), benzene (70 ml) and the dimethyl acetal of 2-chloromethylaminoacetaldehyde (13.5 grams) are charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The reaction mixture is then stirred at room temperature for a period of about 1 hour. After this time the reaction mixture is filtered, and the filtrate is stripped of solvent under reduced pressure, leaving an oil. This oil is dissolved in an ethanol-water mixture, and the solution is filtered. The filtrate is then stripped of solvents under vacuum to yield the desired product the dimethyl acetal of 2-[1-chloromethyl-3-(5-bromothiazol-2-yl)ureido]acetaldehyde.

Workup

  1. customequipped with a mechanical stirrer
  2. filtrationAfter this time the reaction mixture is filtered
  3. customleaving an oil
  4. filtrationthe solution is filtered

Sources & evidence

ORD record
ord-ba9923d7a98843c6a812dfde863c565e
Source dataset
uspto-grants-1978_09
Patent number
US04116969

Reaction notes

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