Pyridine → 2-Acetamino-5-thiocyanatothiazole

HRID 1637232Notes

Reaction equation

HRID 1637232 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. 1H NMR (CD3OD) δ7.79 (s, 1 H), 2.23 (s, 3 H).

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-84ef208f2d754eb486a3255306b66625
Source dataset
uspto-grants-2000_03
Patent number
US06040321

Reaction notes

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