Dimethylamine → HCID 18960564, compound

HRID 1271645Notes

Reaction equation

HRID 1271645 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5](O)=[O:6].C1CC[CH:15]([N:18]=[C:19]=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.CNC>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([N:18]([CH3:19])[CH3:15])=[O:6]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 10868DicyclohexylcarbodiimideHCID 198603-Chloro-4-hydroxybenzoic acidHCID 757711-Hydroxybenzotriazole

Product 1

HCID 18960564HCID 18960564, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Chloro-4-hydroxy-benzoic acid (800 mg, 4.6 mmol), DCC (856 mg, 5.4 mmol), and HOBt (540 mg, 5.4 mmol) were mixed in DMF (10 mL). N,N-dimethyl amine (2M in THF, 4.6 mL) was added to the mixture at 0° C. The reaction was stirred over night and purified by silica gel chromatography (70%–90% EtOAc/Hexane) to provide the title compound (700 mg, 87.5%). MS (DCI) m/z 200, 202 (M+H)+.

Workup

  1. custompurified by silica gel chromatography (70%–90% EtOAc/Hexane)

Sources & evidence

ORD record
ord-39282c94676244f7a7aba4475e7095ef
Source dataset
uspto-grants-2007_04
Patent number
US07205409B2

Reaction notes

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