Pyridine → 2-Acetamino-5-thiocyanatothiazole

HRID 1385186Notes

Reaction equation

HRID 1385186 reaction equation
[NH2:1][C:2]1[S:3][C:4]([S:7][C:8]#[N:9])=[CH:5][N:6]=1.N1C=CC=CC=1.[C:16](OC(=O)C)(=[O:18])[CH3:17]>C(Cl)Cl>[C:16]([NH:1][C:2]1[S:3][C:4]([S:7][C:8]#[N:9])=[CH:5][N:6]=1)(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 3109677[(2-Amino-1,3-thiazol-5-yl)sulfanyl]formonitrile

Product 1

HCID 153463412-Acetamino-5-thiocyanatothiazoleYield 76.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-amino-5-thiocyanatothiazole (15.7 g, 0.1 mol) and pyridine (12 g, 0.15 mol) in methylene chloride (100 mL) was added acetic anhydride (1.2 g, 0.12 mol) at rt. The mixture was stirred at rt for 6 h. The mixture was concentrated to dryness and to the residue MeOH (50 mL) was added. The precipitates were collected and washed with water. The solid was dried and recrystallized from MeOH to afford 2-acetylamino-5-thiocyanatothiazole (15.2 g, 76%) as a solid, mp 212° C.

Workup

  1. concentrationThe mixture was concentrated to dryness and to the residue MeOH (50 mL)
  2. additionwas added
  3. customThe precipitates were collected
  4. washwashed with water
  5. customThe solid was dried
  6. customrecrystallized from MeOH

Sources & evidence

ORD record
ord-cab8b251d4094444a965f381d7344ba8
Source dataset
uspto-grants-2001_07
Patent number
US06262096B1

Reaction notes

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