Isopropylamine → 2-Chloro-thiazole-5-carboxylic acid isopropylamide

HRID 1923645Notes

Reaction equation

HRID 1923645 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].C[Al](C)C.C([O:11][C:12]([C:14]1[S:18][C:17]([Cl:19])=[N:16][CH:15]=1)=O)C>O1CCOCC1.C1(C)C=CC=CC=1>[CH:1]([NH:4][C:12]([C:14]1[S:18][C:17]([Cl:19])=[N:16][CH:15]=1)=[O:11])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6363IsopropylamineHCID 16682925TrimethylaluminumHCID 19017727Ethyl 2-chloro-1,3-thiazole-5-carboxylate

Product 1

HCID 666437382-Chloro-thiazole-5-carboxylic acid isopropylamideYield 94%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
90 °C

Procedure

To a stirred solution of isopropylamine (123 mg, 2.08 mmol) in dioxane (5 mL) under argon and at room temperature was added trimethylaluminium (1.04 mL of a 2M solution in toluene, 2.08 mmol). After 1 h, a solution of 2-chloro-thiazole-5-carboxylic acid ethyl ester (100 mg, 0.522 mmol) in dioxane (5 mL) was added and the reaction mixture warmed to 90° C. After 6 h, the reaction mixture was cooled, quenched with Seignettes's salt solution and water, then extracted with dichloromethane. The combined organic extracts were dried, filtered and concentrated. Purification by chromatography (silica, 0 to 30% ethyl acetate in heptane) gave the title compound (100 mg, 94%) as a white solid. MS: m/e=203.4 [M+H]+.

Workup

  1. waitAfter 6 h
  2. temperaturethe reaction mixture was cooled
  3. customquenched with Seignettes's salt solution and water
  4. extractionextracted with dichloromethane
  5. customThe combined organic extracts were dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by chromatography (silica, 0 to 30% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-20cf030f0bec4b029a833ced77cbe858
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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