Stearoyl chloride → HCID 9890245, compound

HRID 1532673Notes

Reaction equation

HRID 1532673 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]([CH3:22])[CH2:10][CH2:11][CH2:12][NH:13][C:14]1[C:15]([NH2:21])=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=1.[C:23](Cl)(=O)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]>ClCCl>[CH2:39]([C:40]1[N:13]([CH2:12][CH2:11][CH2:10][N:9]([CH3:8])[CH3:22])[C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=2[N:21]=1)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH3:23]

Participants

5

Reactant 3

HCID 8212Stearoyl chlorideHCID 8471TriethylamineHCID 43168878HCID 43168878, compound

Product 1

HCID 9890245HCID 9890245, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Triethylamine (0.557 g) was added to a solution containing N1-[3-(dimethylamino)propyl]4-methyl-1,2-benzenediamine (1.037 g) in dichloromethane (5 ml), and then a solution containing stearoyl chloride (1.515 g) in dichloromethane (5 mnl) was added thereto while being cooled with ice. After being stirred for 4.5 hours at room temperature, the reaction mixture was diluted with dichloromethane, washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and concentrated. Concentrated hydrochloric acid (3.5 ml) was added to a solution containing the residue (1.97 g) in ethanol (20 ml). After being stiffed for 5.5 hours at 90° C., the reaction mixture was concentrated. The residue, with chloroform added thereto, was washed with 0.5N sodium hydroxide aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and concentrated. The residue (1.03 g) was purified by silica gel column chromatography (silica gel 30 g, chloroform:methanol=50:1-1:1), thereby yielding the entitled compound (0.714 g) as pale yellow solid.

Workup

  1. additionwas added
  2. temperaturewhile being cooled with ice
  3. washwashed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively
  4. dry with materialdried over sodium sulfate anhydride
  5. concentrationconcentrated
  6. additionConcentrated hydrochloric acid (3.5 ml) was added to a solution
  7. additioncontaining the residue (1.97 g) in ethanol (20 ml)
  8. waitAfter being stiffed for 5.5 hours at 90° C.
  9. concentrationthe reaction mixture was concentrated
  10. additionThe residue, with chloroform added
  11. washwas washed with 0.5N sodium hydroxide aqueous solution and saturated brine successively
  12. dry with materialdried over sodium sulfate anhydride
  13. concentrationconcentrated
  14. customThe residue (1.03 g) was purified by silica gel column chromatography (silica gel 30 g, chloroform:methanol=50:1-1:1)

Sources & evidence

ORD record
ord-c2f542b22a724a3a8c965b7d636f0dd3
Source dataset
uspto-grants-2001_03
Patent number
US06204264B1

Reaction notes

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