Triethylamine → 1-[3-(4-Chlorophenyl)-1,2-oxazol-5-yl]methanamine

HRID 1711539Notes

Reaction equation

HRID 1711539 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]=[N:7][OH:8])=[CH:4][CH:3]=1.Cl[N:12]1C(=O)[CH2:15][CH2:14][C:13]1=O.C(N)C#C.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[CH:15]=[C:14]([CH2:13][NH2:12])[O:8][N:7]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 2191584-Chloro-benzaldehyde oximeHCID 239041Propargylamine

Product 1

HCID 27641631-[3-(4-Chlorophenyl)-1,2-oxazol-5-yl]methanamineYield 110.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.56 g (10 mmol) of p-chlorobenzaldoxime was dissolved in 40 ml of dried dichloromethane in a erlenmeyer flask equipped with a magnetic stirrer, and 1.7 g (12 mmol) of N-chlorosuccinimide was added slowly. The reaction mixture was stirred until completely dissolved. The system was heated slightly for 20 min. Then, 0.56 g (10 mmol) of propargyl amine was introduced and 1.2 g (12 mmol) of triethylamine was added dropwise, which caused the emission of white smog. The reaction mixture was heated under reflux for 2 h, and then purified by column chromatography on silica gel using petroleum ether (b.p. 60-90° C.)—ethyl acetate (v:v=4:1) as eluant, to obtain 2.3 g of the product as yellow solid. The yield was 62%.

Workup

  1. customequipped with a magnetic stirrer
  2. dissolutionuntil completely dissolved
  3. temperatureThe system was heated slightly for 20 min
  4. temperatureThe reaction mixture was heated
  5. temperatureunder reflux for 2 h
  6. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-e229fd65466c4afa88552f7c6d1dd472
Source dataset
uspto-grants-2010_09
Patent number
US07790759B2

Reaction notes

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