Water → Isoxazole 9

HRID 216009Notes

Reaction equation

HRID 216009 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:10][N:9]=[C:8]([C:11]([O:13]CC)=O)[CH:7]=1.[CH:16]1([NH2:19])[CH2:18][CH2:17]1.O>C(O)C>[CH:16]1([NH:19][C:11]([C:8]2[CH:7]=[C:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)[O:10][N:9]=2)=[O:13])[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 962WaterHCID 69828CyclopropylamineHCID 2745138Ethyl 5-(thiophen-2-yl)-1,2-oxazole-3-carboxylate

Product 1

HCID 19582717Isoxazole 9Yield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 5-(thiophen-2-yl)isoxazole-3-carboxylate (220 mg, 1 mmol) in absolute ethanol (5 mL) was added cyclopropylamine (285 mg, 5 mmol). The reaction was sealed and heated to 80° C. for 24 hours. The reaction was allowed to cool to room temperature and water (1 mL) was added. The product was collected by vacuum filtration as a white crystalline solid (150 mg, 64% yield). δH (400 MHz, d6 DMSO): 8.85 (1H, d), 7.83 (1H, d), 7.76 (1H, d), 7.24 (1H, d), 7.18 (1H, s), 2.83 (1H, m), 0.58-0.71 (4H, m).

Workup

  1. customThe reaction was sealed
  2. temperatureto cool to room temperature

Sources & evidence

ORD record
ord-8f6a25cd0402464dbebfa8d942bc6cfa
Source dataset
uspto-grants-2012_06
Patent number
US08193225B2

Reaction notes

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