Chloroacetyl chloride → HCID 86603853, compound

HRID 2111506Notes

Reaction equation

HRID 2111506 reaction equation
[CH2:1]([NH2:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C([O-])([O-])=O.[Na+].[Na+].[Cl:26][CH2:27][C:28](Cl)=[O:29]>O>[Cl:26][CH2:27][C:28]([NH:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:29]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chloride2×HCID 10340Sodium Carbonate2×HCID 5356789Oleylamine

Product 1

HCID 86603853HCID 86603853, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
12.5 °C

Procedure

To a rapidly stirred mixture of oleylamine (118.5 g), diether (200 mL), Na2CO3 (50.29 g) and water (500 mL) is added chloroacetyl chloride (54.16 g) dropwise over 60 min. Intermittent cooling is applied to maintain temperature between 10-15° C. After completion of addition, the mixture is stirred for 60 min, and the phases are allowed to separate. Analysis (H-NMR) of a sample of the upper ether layer indicates that a small amount of amine is not reacted. Additional Na2CO3 (7 g) and water (50 mL) is added, followed by chloroacetyl chloride (7 g). The upper ether phase is removed, the aqueous phase extracted with additional ether (200 mL), and the combined organic phase is washed with water (2×125 mL portions), saturated NaCl (125 mL), dried over anh. Na2SO4, and the solvent removed in vacuo to give 149 g of 2-chloro-N-oleylacetamide.

Workup

  1. temperatureIntermittent cooling
  2. additionAfter completion of addition
  3. customto separate
  4. customis not reacted
  5. customThe upper ether phase is removed
  6. extractionthe aqueous phase extracted with additional ether (200 mL)
  7. washthe combined organic phase is washed with water (2×125 mL portions), saturated NaCl (125 mL)
  8. dry with materialdried over anh. Na2SO4
  9. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-389451ac4d02421cb034c60a0a5bae0f
Source dataset
uspto-grants-2009_04
Patent number
US07521403B2

Reaction notes

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