Isopropanol → 7-Diethylamino-3-(4-phenylthiazol-2-yl)-iminocoumarin

HRID 1995449Notes

Reaction equation

HRID 1995449 reaction equation
[CH2:1]([N:3]([CH2:13][CH3:14])[C:4]1[CH:5]=[C:6]([OH:12])[C:7](=[CH:10][CH:11]=1)C=O)[CH3:2].[C:15]([CH2:17][C:18]1[S:19][CH:20]=[C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:22]=1)#[N:16].N1CCCC1.[CH:34]([OH:37])(C)C>>[CH2:13]([N:3]([CH2:1][CH3:2])[C:4]1[CH:5]=[C:6]2[C:7]([C:15](=[NH:16])[CH:17]([C:18]3[S:19][CH:20]=[C:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[N:22]=3)[C:34](=[O:37])[O:12]2)=[CH:10][CH:11]=1)[CH3:14]

Participants

5

Reactant 4

HCID 3776IsopropanolHCID 31268PyrrolidineHCID 872934-(Diethylamino)-2-hydroxybenzaldehydeHCID 704539(4-Phenyl-1,3-thiazol-2-yl)acetonitrile

Product 1

HCID 867390267-Diethylamino-3-(4-phenylthiazol-2-yl)-iminocoumarinYield 81.3%

Procedure

3.9 parts of 4-diethylaminosalicylaldehyde and 4 parts of 2-cyanomethyl-4-phenyl-thiazole in 40 parts by volume of isopropyl alcohol are refluxed with 0.5 part by volume of pyrrolidine for 1 hour. The reaction mixture is then cooled and the precipitate is filtered off and washed. 6.1 parts (81.3% of theory) of 7-diethylamino-3-(4-phenylthiazol-2-yl)-iminocoumarin, of melting point120°-128° C., are obtained.

Workup

  1. temperatureThe reaction mixture is then cooled
  2. filtrationthe precipitate is filtered off
  3. washwashed

Sources & evidence

ORD record
ord-26ac398c4c40419f9ba7740429bea8d6
Source dataset
uspto-grants-1983_09
Patent number
US04404389

Reaction notes

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