Palmitoyl chloride → HCID 15006861, compound

HRID 2164857Notes

Reaction equation

HRID 2164857 reaction equation
C([O:3][C:4]1[CH:9]=[CH:8][C:7]([O:10]CC)=[CH:6][C:5]=1[NH:13][C:14](=[O:30])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])C.C(OC1C=CC(OCC)=CC=1N)C.C(Cl)(=O)CCCCCCCCCCCCCCC.B(Br)(Br)Br>C(Cl)(Cl)Cl.O>[C:14]([NH:13][C:5]1[CH:6]=[C:7]([OH:10])[CH:8]=[CH:9][C:4]=1[OH:3])(=[O:30])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

7

Reactant 4

HCID 8206Palmitoyl chlorideHCID 25134Boron tribromideHCID 66756Benzenamine, 2,5-diethoxy-HCID 20403382HCID 20403382, compound

Product 1

HCID 15006861HCID 15006861, compoundYield 107.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

83.8 g (0.2 mol) of 1,4-diethoxy-2-hexadecanoylaminobenzene prepared from 2,5-diethoxyaniline and hexadecanoyl chloride was dissolved in 500 ml of chloroform and to the solution was added dropwise 100 g of boron tribromide at a temperature range between 5° C. and 10° C. After stirring at room temperature for 6 hours, 50 g of ice and 100 ml of water were added to the mixture and chloroform was distilled off under a reduced pressure. To the residue was added 100 ml of methanol, the resulting precipitate was collected by filtration to obtain 78 g of 2-hexadecanoylaminohydroquinone.

Workup

  1. distillationwas distilled off under a reduced pressure
  2. additionTo the residue was added 100 ml of methanol
  3. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-e630fd0b1d9245ff8629039304ee9831
Source dataset
uspto-grants-1985_03
Patent number
US04507380

Reaction notes

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