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

HRID 870879Notes

Reaction equation

HRID 870879 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]>C(O)(C)C>[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 84.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
25 °C

Procedure

Isopropyl alcohol (50 mL) was placed into a round bottom flask and 3-cyano-4-isobutoxybenzothioamide (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 the solid was washed with isopropyl alcohol (10 mL). The wet solid was dried at about 75° C. to a constant weight to yield 6.2 g of the title compound. Purity by HPLC: 98.31%.

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. washthe solid was washed with isopropyl alcohol (10 mL)
  7. customThe wet solid was dried at about 75° C. to a constant weight

Sources & evidence

ORD record
ord-5aa2860618d2462fb66e22bf64d10c50
Source dataset
uspto-grants-2015_03
Patent number
US08969582B2

Reaction notes

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