Ethyl 2-chloroacetoacetate → 5-Thiazolecarboxylic acid, 2-(3-cyano-4-(2-methylpropoxy)phenyl)-4-methyl-, ethyl ester

HRID 870882Notes

Reaction equation

HRID 870882 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH:14]([CH3:16])[CH3:15])[C:6](=[S:8])[NH2:7])#[N:2].[CH2:17]([O:19][C:20](=[O:26])[CH:21](Cl)[C:22]([CH3:24])=O)[CH3:18]>CO>[C:1]([C:3]1[CH:4]=[C:5]([C:6]2[S:8][C:21]([C:20]([O:19][CH2:17][CH3:18])=[O:26])=[C:22]([CH3:24])[N:7]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH:14]([CH3:16])[CH3:15])#[N:2]

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 117703963-Cyano-4-isobutoxybenzothioamide

Product 1

HCID 98845495-Thiazolecarboxylic acid, 2-(3-cyano-4-(2-methylpropoxy)phenyl)-4-methyl-, ethyl esterYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

Methanol (50 mL) was placed into a round bottom flask and 3-cyano-4-isobutoxy benzothioamide (5.0 g) was added, followed by addition of ethyl-2-chloroacetoacetate (4.25 g). The mixture was heated to reflux and maintained until reaction completion. After the reaction was completed, the mass was cooled to about 25° C. and maintained for about 30 minutes. The mass was then filtered and washed with methanol. The wet solid was dried at about 70° C. to a constant weight to yield 5.0 g of the title compound. Purity by HPLC: 84.9%.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperaturemaintained until reaction completion
  4. temperaturemaintained for about 30 minutes
  5. filtrationThe mass was then filtered
  6. washwashed with methanol
  7. customThe wet solid was dried at about 70° C. to a constant weight

Sources & evidence

ORD record
ord-f1bb12a62c2746c88d31279488e20f7c
Source dataset
uspto-grants-2015_03
Patent number
US08969582B2

Reaction notes

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