Hydrochloric Acid → [2-(3-Amino-propylamino)-thiazol-5-yl]-o-tolyl-methanone

HRID 2119606Notes

Reaction equation

HRID 2119606 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]1[S:13][C:14]([C:17](=[O:25])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])=[CH:15][N:16]=1)(C)(C)C.Cl.C(=O)(O)[O-].[Na+]>O1CCOCC1>[NH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]1[S:13][C:14]([C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])=[O:25])=[CH:15][N:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 20616905{3-[5-(2-Methyl-benzoyl)-thiazol-2-ylamino]-propyl}-carbamic Acid tert-butyl Ester

Product 1

HCID 23442548[2-(3-Amino-propylamino)-thiazol-5-yl]-o-tolyl-methanoneYield 102.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

339 mg {3-[5-(2-Methyl-benzoyl)-thiazol-2-ylamino]-propyl}-carbamic acid tert-butyl ester was added to a solution of 25% aqueous hydrochloric acid in dioxane. The mixture was stirred 1 h at room temperature and maintained overnight in the refrigerator. The mixture was poured into saturated aqueous sodium bicarbonate solution (50 ml). The organics were extracted with dichloromethane (3×50 ml), dried over magnesium sulfate and evaporated under reduced pressure to afford the title compound as yellow foam (254 mg) which was used without further purification.

Workup

  1. temperaturemaintained overnight in the refrigerator
  2. extractionThe organics were extracted with dichloromethane (3×50 ml)
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e5002b6f0d2f4f38949d84439ff9188f
Source dataset
uspto-grants-2004_02
Patent number
US06686381B2

Reaction notes

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