(2-Amino-1,3-thiazol-4-yl)acetic acid → HCID 23512079, compound

HRID 354469Notes

Reaction equation

HRID 354469 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([OH:10])=[O:9])[N:6]=1.[C:11]1([CH3:20])[C:12]([N:17]=[C:18]=[O:19])=[CH:13][CH:14]=[CH:15][CH:16]=1>CC(C)=O>[C:11]1([CH3:20])[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH:17][C:18](=[O:19])[NH:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([OH:10])=[O:9])[N:6]=1

Participants

4

Reactant 2

HCID 34665(2-Amino-1,3-thiazol-4-yl)acetic acidHCID 691942-Tolyl isocyanate

Product 1

HCID 23512079HCID 23512079, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 2-amino-4-thiazoleacetic acid (4 g, 25 mmol) in 1:1 CH2Cl:acetone (100 mL) was added o-tolylisocyanate (3.5 g, 26 mmol). The mixture was heated to reflux for 8 hr at which time a yellow precipitate had formed the precipitate was filtered and the solid washed generously with 1:1 CH2Cl2:acetone. The solid was recrystallized with hot methanol and dried under vacuum to yield 4.8 g (66% yield) of the desired 2-(o-tolylureido)-4-thiazoleacetic acid 225.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 8 hr at which time a yellow precipitate
  3. customhad formed the precipitate
  4. filtrationwas filtered
  5. washthe solid washed generously with 1:1 CH2Cl2
  6. customThe solid was recrystallized with hot methanol
  7. customdried under vacuum

Sources & evidence

ORD record
ord-0f14b74d110b448f83f7ac577ffbb744
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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