Water → HCID 86722255, compound

HRID 869409Notes

Reaction equation

HRID 869409 reaction equation
[C:1]([C:4]1[O:5][C:6]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([Br:16])[C:7]=2[C:8]=1[NH2:9])(=[O:3])[CH3:2].[CH:17]([C:20]1[S:21][C:22]([CH:25]=O)=[CH:23][N:24]=1)([CH3:19])[CH3:18].[OH-].[Na+].O>C1COCC1>[NH2:9][C:8]1[C:7]2[C:10]([Br:16])=[C:11]([O:14][CH3:15])[CH:12]=[CH:13][C:6]=2[O:5][C:4]=1[C:1](=[O:3])/[CH:2]=[CH:25]/[C:22]1[S:21][C:20]([CH:17]([CH3:19])[CH3:18])=[N:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 450838485-Thiazolecarboxaldehyde, 2-(1-methylethyl)- (9CI)HCID 86722252HCID 86722252, compound

Product 1

HCID 86722255HCID 86722255, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 12G (1.5 g, 5.2 mmol), 2-isopropyl-thiazole-5-carbaldehyde (1.2 g, 7.7 mmol) in THF (20 mL) was cooled to 0° C. To the mixture was added NaOH (1.5 g), then stirred at room temperature overnight. TLC monitored the reaction. After the reaction completed, the reaction mixture was added dropwise into water. The precipitated solids were collected by filtration to give 14A (1.4 g, 62.9% yield).

Workup

  1. customthe reaction
  2. filtrationThe precipitated solids were collected by filtration

Sources & evidence

ORD record
ord-bb860ab867aa427797ee077a286a45ca
Source dataset
uspto-grants-2015_03
Patent number
US08969373B2

Reaction notes

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