Formic Acid → HCID 20544502, compound

HRID 2285793Notes

Reaction equation

HRID 2285793 reaction equation
Cl.[NH2:2]O.[NH2:4][C:5]1[S:6][C:7]([CH:10]=O)=[CH:8][N:9]=1.[CH:12]([O-:14])=O.[Na+].C(O)=O>CO.C(Cl)(Cl)Cl>[C:10]([C:7]1[S:6][C:5]([NH:4][CH:12]=[O:14])=[N:9][CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 443297Hydroxyamine hydrochlorideHCID 2723810Sodium FormateHCID 27377982-Amino-1,3-thiazole-5-carbaldehyde

Product 1

HCID 20544502HCID 20544502, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

Hydroxylamine hydrochloride (24.0 g, 0.30 m+15% molar excess), crude 2-amino-5-formylthiazole (38.4 g, 0.30 m), and sodium formate (37.5 g, 0.55 m) are combined in 450 ml of 97% (commercial) formic acid. The mixture is heated on a steam bath until TLC (10% CH3OH/CHCl3) shows only a single product spot (about 7-8 hr.). The reaction mixture is filtered hot and the filtrate condensed under reduced pressure. The residue is triturated in ice water, the solid collected by filtration, washed with water, and air-dried to yield 27.7 g (0.18 m, 60.5%) of 5-cyano-2-formamidothiazole as a reddish-brown powder.

Workup

  1. customa single product spot (about 7-8 hr.)
  2. filtrationThe reaction mixture is filtered hot
  3. customthe filtrate condensed under reduced pressure
  4. customThe residue is triturated in ice water
  5. filtrationthe solid collected by filtration
  6. washwashed with water
  7. customair-dried

Sources & evidence

ORD record
ord-115f920ffd624fe3a42a5da61bfcedfe
Source dataset
uspto-grants-1982_04
Patent number
US04324899

Reaction notes

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