Sodium Hydroxide → 5-Amino-3-methyl-1,2-oxazole-4-carbonitrile

HRID 1794591Notes

Reaction equation

HRID 1794591 reaction equation
Cl.[NH2:2][OH:3].[OH-].[Na+].C(O[C:9](=[C:11]([C:14]#[N:15])[C:12]#[N:13])[CH3:10])C>O>[NH2:13][C:12]1[O:3][N:2]=[C:9]([CH3:10])[C:11]=1[C:14]#[N:15]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 79450(1-Ethoxyethylidene)malononitrileHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 3055905-Amino-3-methyl-1,2-oxazole-4-carbonitrileYield 72.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of hydroxylamine hydrochloride (27.8 g, 0.4 mol) and sodium hydroxide (16.0 g, 0.4 mol) in water (1000 mL) was treated with 2-(1-ethoxy-ethylidene)-malononitrile (54.42 g, 0.4 mol) over 1 h. After the addition, the reaction mixture was stirred at room temperature for 18 h. The resulting suspension was collected, washed with cold EtOAc (1000 mL) and air dried to afford the desired product as a white solid (35.8 g, 72%); 1H NMR (DMSO-d6) δ 8.32 (s, 2 H), 2.1 (s, 3H).

Workup

  1. additionAfter the addition
  2. customThe resulting suspension was collected
  3. washwashed with cold EtOAc (1000 mL) and air
  4. customdried

Sources & evidence

ORD record
ord-6fd0c6a3829b4d8c906e7d4c1c80f8fb
Source dataset
uspto-grants-2006_04
Patent number
US07022850B2

Reaction notes

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