Triethylamine → N-(4-bromobenzyl)-2,6-dichloro-4-(2-methoxyethoxy)benzamide

HRID 2038341Notes

Reaction equation

HRID 2038341 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[CH:8]=[C:7]([Cl:16])[C:3]=1[C:4]([OH:6])=O.Cl.[Br:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][NH2:26])=[CH:21][CH:20]=1.C[NH3+].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[Br:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][NH:26][C:4](=[O:6])[C:3]2[C:7]([Cl:16])=[CH:8][C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[CH:10][C:2]=2[Cl:1])=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 27240964-Bromobenzylamine hydrochlorideHCID 711500392,6-Dichloro-4-(2-methoxyethoxy)benzoic acidHCID 866211442-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate Methanaminium

Product 1

HCID 71149974N-(4-bromobenzyl)-2,6-dichloro-4-(2-methoxyethoxy)benzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,6-Dichloro-4-(2-methoxyethoxy)benzoic acid (0.1 g, 0.23 mmol), (4-bromophenyl)methanamine hydrochloride (0.1 g, 0.27 mmol), 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate methanaminium (HATU) (0.17 g, 0.27 mmol), and triethylamine (0.15 mL, 0.7 mmol) were combined in DMF (3 mL) and then stirred at room temperature until reaction was completed. The reaction mixture was diluted with ethyl acetate and washed with water and twice with a saturated sodium bicarbonate solution. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuum. The solid resulting was used for next step without further purification.

Workup

  1. washwashed with water and twice with a saturated sodium bicarbonate solution
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuum
  5. customThe solid resulting
  6. customwas used for next step without further purification

Sources & evidence

ORD record
ord-ee062072585f468fa2841d92f745c9ae
Source dataset
uspto-grants-2013_11
Patent number
US08575353B2

Reaction notes

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