Palmitoyl chloride → Palmitic acid N-hydroxysuccinimide

HRID 1464855Notes

Reaction equation

HRID 1464855 reaction equation
[C:1](Cl)(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[OH:19][N:20]1[C:24](=[O:25])[CH2:23][CH2:22][C:21]1=[O:26].C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:1]([O:19][N:20]1[C:24](=[O:25])[CH2:23][CH2:22][C:21]1=[O:26])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 8206Palmitoyl chlorideHCID 8471TriethylamineHCID 80170N-Hydroxysuccinimide

Product 1

HCID 4620598Palmitic acid N-hydroxysuccinimide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 165 mL (0.544 mol) of palmitoyl chloride in 1 L of chloroform while cooled with ice with stirring, 69.8 g (0.598 mol) of N-hydroxysuccinimide was gradually added, and 83.1 mL (0.598 mol) of triethylamine was added dropwise thereto over 30 minutes. The resultant solution was stirred for 30 minutes while cooled with ice and for another 7 hours during which the resultant solution gradually reached room temperature. After washed with 500 mL of water three times, the resultant solution was dried over magnesium sulfate and was then concentrated under reduced pressure to obtain 260.3 g (quant) of a colorless solid.

Workup

  1. washAfter washed with 500 mL of water three times
  2. dry with materialthe resultant solution was dried over magnesium sulfate
  3. concentrationwas then concentrated under reduced pressure
  4. customto obtain 260.3 g (quant) of a colorless solid

Sources & evidence

ORD record
ord-49af15b57400451182352f8dced080b7
Source dataset
uspto-grants-2015_04
Patent number
US08999300B2

Reaction notes

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