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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-bromo-2-chloro-N-(2,2-diethoxyethyl)benzamide

HRID 394854
Notes
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Reaction equation

HRID 394854 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH2:12]([O:14][CH:15]([O:18][CH2:19][CH3:20])[CH2:16][NH2:17])[CH3:13].CCN=C=NCCCN(C)C>C(Cl)Cl>[Br:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([NH:17][CH2:16][CH:15]([O:18][CH2:19][CH3:20])[O:14][CH2:12][CH3:13])=[O:6])=[C:2]([Cl:1])[CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 695242,2-DiethoxyethylamineHCID 1088294-Bromo-2-chlorobenzoic acid

Product 1

HCID 223137884-bromo-2-chloro-N-(2,2-diethoxyethyl)benzamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-chloro-4-bromobenzoic acid (10.0 g, 42.47 mmol) in CH2Cl2 (1000 mL) was added aminoacetaldehyde diethyl acetal (5.1 mL, 46.72 mmol) and WSC (9.77 g, 50.96 mmol) at room temperature, and stirred for 4 hours. The mixture was washed with water (100 mL), dried over MgSO4. Removal of the solvent, gave title compound (14.88 g, 100% yield).

Workup

  1. washThe mixture was washed with water (100 mL)
  2. dry with materialdried over MgSO4
  3. customRemoval of the solvent

Sources & evidence

ORD record
ord-9971407d6b864fc4865cbb0413c988fb
Source dataset
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06603008B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes