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Phosphorus oxychloride → 4-Isopropyl-thiazole-2-carboxylic acid [6-acetyl-2-chloro-3-(2,2-dimethoxy-ethoxy)-phenyl]-amide

HRID 1422529
Notes
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Reaction equation

HRID 1422529 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9][CH2:10][CH:11]([O:14][CH3:15])[O:12][CH3:13])[CH:5]=[CH:4][C:3]=1[C:16](=[O:18])[CH3:17].[CH:19]([C:22]1[N:23]=[C:24]([C:27](O)=[O:28])[S:25][CH:26]=1)([CH3:21])[CH3:20].O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[C:16]([C:3]1[C:2]([NH:1][C:27]([C:24]2[S:25][CH:26]=[C:22]([CH:19]([CH3:21])[CH3:20])[N:23]=2)=[O:28])=[C:7]([Cl:8])[C:6]([O:9][CH2:10][CH:11]([O:12][CH3:13])[O:14][CH3:15])=[CH:5][CH:4]=1)(=[O:18])[CH3:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 224993072-Thiazolecarboxylic acid, 4-(1-methylethyl)-HCID 574451961-[2-Amino-3-chloro-4-(2,2-dimethoxy-ethoxy)-phenyl]-ethanone

Product 1

HCID 672246774-Isopropyl-thiazole-2-carboxylic acid [6-acetyl-2-chloro-3-(2,2-dimethoxy-ethoxy)-phenyl]-amideYield 96.1%

Reagents, catalysts & solvents 1

HCID 1049
Pyridine
Solvent

Conditions

Temperature
-10 °C

Procedure

1-[2-amino-3-chloro-4-(2,2-dimethoxy-ethoxy)-phenyl]-ethanone (1.89 g, 6.92 mmol) and 4-isopropyl-thiazole-2-carboxylic acid (1.77 g, 10.38 mmol) was dissolved in pyridine (20 mL) and was cooled to −10° C. POCl3 (0.823 mL, 8.99 mmol) was added dropwise. The reaction was stirred at −10° C. for 2 hours. The reaction was quenched with CH3OH (5 mL). After 15 minutes, the reaction was taken up in EtOAc and extracted with 2N HCl(aq). The organic layer was dried with Na2SO4, filtered and was concentrated. 4-Isopropyl-thiazole-2-carboxylic acid [6-acetyl-2-chloro-3-(2,2-dimethoxy-ethoxy)-phenyl]-amide (2.84 g, 96%) was isolated by silica gel chromatography as a white solid.

Workup

  1. customThe reaction was quenched with CH3OH (5 mL)
  2. waitAfter 15 minutes
  3. extractionextracted with 2N HCl(aq)
  4. dry with materialThe organic layer was dried with Na2SO4
  5. filtrationfiltered
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-a1a00cbbf35846ec8f7960fda113f412
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08927484B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes