2-Aminothiazole → 2-cyano-N-(1,3-thiazol-2-yl)acetamide

HRID 1903098Notes

Reaction equation

HRID 1903098 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].[NH2:7][C:8]1[S:9][CH:10]=[CH:11][N:12]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(#N)C.[OH-].[Na+]>[C:1]([CH2:3][C:4]([NH:7][C:8]1[S:9][CH:10]=[CH:11][N:12]=1)=[O:6])#[N:2]

Participants

6

Reactant 3

HCID 21552-AminothiazoleHCID 9740Cyanoacetic acidHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 6931662-cyano-N-(1,3-thiazol-2-yl)acetamide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent3×HCID 14798Sodium HydroxideSolvent

Procedure

4.5 g of cyanoacetic acid and 5.3 g of 2-aminothiazole, each in acetonitrile were combined, and the suspension (60 ml) was treated with a solution of 12.0 g of dicyclohexylcarbodiimide in 30 ml of acetonitrile. After exothermic reaction (and solidification) additional acetonitrile (60 ml) was added and the mixture stirred 1 hr and let stand overnight. The collected solid (20 g) was stirred with dilute (ca. 2%) NaOH solution and filtered. The filtrate was acidified with 6 N HCl and the product collected, washed with water, dried (m.p. 229°-230°) and recrystallized from acetone to give 2-(cyanoacetylamino)thiazole, m.p. 231°-2° dec.

Workup

  1. additionwas added
  2. waitlet stand overnight
  3. filtrationfiltered
  4. customthe product collected
  5. washwashed with water
  6. customdried (m.p. 229°-230°)
  7. customrecrystallized from acetone

Sources & evidence

ORD record
ord-7aed9a92fe354bd6b93832256714feb2
Source dataset
uspto-grants-1984_03
Patent number
US04435407

Reaction notes

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