Triethylamine → HCID 86593926, compound

HRID 2114988Notes

Reaction equation

HRID 2114988 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7](=[S:9])[O:8][C:4]=2[CH:3]=1.C(N(CC)CC)C.[CH2:19]([CH:26]1[CH2:31][CH2:30][N:29]([C:32](=[O:36])[C:33](Cl)=[O:34])[CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)(Cl)Cl>[CH2:19]([CH:26]1[CH2:27][CH2:28][N:29]([C:32](=[O:36])[C:33]([NH:1][C:2]2[CH:11]=[CH:10][C:5]3[NH:6][C:7](=[S:9])[O:8][C:4]=3[CH:3]=2)=[O:34])[CH2:30][CH2:31]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 136273456-Amino-1,3-benzoxazole-2(3H)-thioneHCID 16110249HCID 16110249, compound

Product 1

HCID 86593926HCID 86593926, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of 0.3 g (1.8 mmol) of 6-amino-3H-benzoxazole-2-thione [J. Org. Chem., 19; 758. (1954)] and 0.6 ml (4.3 mmol) of triethylamine in 20 ml of chloroform 0.5 g (1.8 mmol) of (4-benzyl-piperidine-1-yl)-oxo-acetyl chloride (Example 38c) in 10 ml of chloroform is added dropwise at 0° C. The reaction mixture is stirred at room temperature for 1 hour, then washed with water and the organic layer is concentrated. The residue is purified by column chromatography using Kieselgel 60 (Merck) as adsorbent and toluene:methanol=4:1 as eluent to yield 0.46 g (61.9%) of the title compound. Melting Point: 203° C. (isopropanol)

Workup

  1. washwashed with water
  2. concentrationthe organic layer is concentrated
  3. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-db05cfc681a14972af70efff1624ced7
Source dataset
uspto-grants-2008_10
Patent number
US07435744B2

Reaction notes

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