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

HRID 2282290Notes

Reaction equation

HRID 2282290 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-f719fa3108f04da39083db2a24b19c51
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

Loading…