Allylamine → N-Allyl-2-bromo-4-(2,4-dichlorophenyl)-1,3-thiazole-5-carboxamide

HRID 1530128Notes

Reaction equation

HRID 1530128 reaction equation
[Br:1][C:2]1[S:3][C:4]([C:15]([OH:17])=O)=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=2[Cl:14])[N:6]=1.C1C=[CH:20][C:21]2N(O)N=[N:24][C:22]=2C=1.Cl.CN(C)CCCN=C=NCC.C(N)C=C>ClCCl.O>[CH2:22]([NH:24][C:15]([C:4]1[S:3][C:2]([Br:1])=[N:6][C:5]=1[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[Cl:14])=[O:17])[CH:21]=[CH2:20]

Participants

7

Reactant 4

HCID 7853AllylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 580948542-Bromo-4-(2,4-dichlorophenyl)-1,3-thiazole-5-carboxylic acid

Product 1

HCID 58095128N-Allyl-2-bromo-4-(2,4-dichlorophenyl)-1,3-thiazole-5-carboxamideYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-Bromo-4-(2,4-dichlorophenyl)-1,3-thiazole-5-carboxylic acid (3.42 g, 9.69 mmol) in dichloromethane (59 mL) was added HOBT.H2O (1.48 g, 9.69 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (2.97 g, 15.5 mmol) followed by 2-propen-1-amine (2.91 mL, 38.8 mmol) and the solution was stirred at room temperature for 16 hours. The solution was then diluted with water and the layers were separated. The organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Column chromatography was performed to yield the title compound (3.11 g, 82%). LCMS: (AA) ES+, 393. 1H NMR (400 MHz, d1-chloroform) δ: 7.57-7.56 (m, 1H), 7.46-7.39 (m, 2H), 5.75-5.65 (m, 1H), 5.43 (br s, 1H), 5.10-5.06 (m, 1H), 5.00-4.94 (m, 1H), 3.88-3.84 (m, 2H).

Workup

  1. customthe layers were separated
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e673542daa8c4f64b17253803255daf7
Source dataset
uspto-grants-2015_07
Patent number
US09090601B2

Reaction notes

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