6-Aminohexanoic Acid → 6-Acrylamidohexanoic Acid

HRID 2100240Notes

Reaction equation

HRID 2100240 reaction equation
[OH-].[Na+].[NH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10].[C:12](Cl)(=[O:15])[CH:13]=[CH2:14]>O.C(Cl)Cl>[C:12]([NH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10])(=[O:15])[CH:13]=[CH2:14]

Participants

6

Reactant 3

HCID 5646-Aminohexanoic AcidHCID 13140Acryloyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 3242006-Acrylamidohexanoic AcidYield 82.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium hydroxide (7.6 g, 190 mmol) and 6-aminohexanoic acid (10 g, 76 mmol) were dissolved in distilled water (50 mL) at room temperature. Acryloyl chloride (8.24 g, 91 mmol) in dry CH2Cl2 (50 mL) was slowly added to the mixture at room temperature. The resulting mixture was stirred at room temperature for 10 h. The reaction was quenched by adding 10% HCl (20 mL, pH 3) at room temperature and the mixture was extracted with ethyl acetate (2×100 mL). The combined organic layers were dried over MgSO4 and concentrated to give a product as a white solid (11.6 g, 82%). This compound was used without further purification.

Workup

  1. customThe reaction was quenched
  2. additionby adding 10% HCl (20 mL, pH 3) at room temperature
  3. extractionthe mixture was extracted with ethyl acetate (2×100 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8ddd5a4339564decb33e094084a0794b
Source dataset
uspto-grants-2009_08
Patent number
US07572644B2

Reaction notes

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