5-Bromo-2-chlorobenzoic acid → 5-bromo-2-chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamide

HRID 2298061Notes

Reaction equation

HRID 2298061 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.C(Cl)(=O)C(Cl)=O.C(N(C(C)C)CC)(C)C.[C:27]12([CH2:37][NH2:38])[CH2:36][CH:31]3[CH2:32][CH:33]([CH2:35][CH:29]([CH2:30]3)[CH2:28]1)[CH2:34]2>CN(C)C=O.ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([NH:38][CH2:37][C:27]12[CH2:36][CH:31]3[CH2:30][CH:29]([CH2:35][CH:33]([CH2:32]3)[CH2:34]1)[CH2:28]2)=[O:9]

Participants

7

Reactant 4

HCID 331275-Bromo-2-chlorobenzoic acidHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamine

Product 1

HCID 79213085-bromo-2-chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Prepared as in Example 1a from 5-bromo-2-chlorobenzoic acid (7.17 g), oxalyl chloride (5.3 ml), dichloromethane (150 ml), dimethylformamide (0.05 ml), diisopropylethylamine (6 ml) and adamantylmethylamine (5 ml) to give the subtitle compound as white colourless needles (7.3 g).

Sources & evidence

ORD record
ord-61171889229146e6a0560ce34325b04c
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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