1-Amino-2-propanol → HCID 43391001, compound

HRID 1672818Notes

Reaction equation

HRID 1672818 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[NH2:11][CH2:12][CH:13]([OH:15])[CH3:14].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>ClCCl.C(Cl)(Cl)Cl>[OH:15][CH:13]([CH3:14])[CH2:12][NH:11][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([I:1])[CH:3]=1

Participants

7

Reactant 4

HCID 41-Amino-2-propanolHCID 120603-Iodobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 43391001HCID 43391001, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

3-Iodobenzoic acid (2.00 g, 8.06 mmol) was dissolved in dichloromethane (80 mL), and the mixture was stirred at room temperature for 2 hours after adding 1-amino-2-propanol (1.25 mL, 16.1 mmol), 1-ethyl-3-(3dimethylaminopropyl)carbodiimide hydrochloride (1.86 g, 9.67 mmol), and 1-hydroxybenzotriazole.monohydrate (1.23 g, 8.06 mmol). The mixture was diluted with chloroform, and washed with a saturated aqueous sodium bicarbonate solution. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and crystallized from diethyl ether to give N-(2-hydroxypropyl)-3-iodobenzamide (1.71 g, 70%).

Workup

  1. washwashed with a saturated aqueous sodium bicarbonate solution
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-b3688cc760874515a4d1660733d8fa49
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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