Stearoyl chloride → HCID 9849308, compound

HRID 1532669Notes

Reaction equation

HRID 1532669 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=1[NH:20][CH2:21][CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])[C:12]([N:14]([CH3:16])[CH3:15])=[O:13].[C:27](Cl)(=O)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]>C(Cl)(Cl)Cl>[CH3:26][N:24]([CH3:25])[CH2:23][CH2:22][CH2:21][N:20]1[C:19]2[CH:18]=[CH:17][C:11]([C:12]([N:14]([CH3:16])[CH3:15])=[O:13])=[CH:10][C:9]=2[N:8]=[C:44]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH3:27]

Participants

5

Reactant 3

HCID 8212Stearoyl chlorideHCID 8471TriethylamineHCID 22013764HCID 22013764, compound

Product 1

HCID 9849308HCID 9849308, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Triethylamine (1.46 ml) was added to a solution containing 3-amino-4-{[3-(dimethylamino)propyl]amino}-N,N-dimethylbenzamide (2.57 g) in chloroform (20 ml), and then stearoyl chloride (2.89 g) was added thereto while being cooled with ice. After being stirred for 2 hours at room temperature, the reaction mixture was diluted with chloroform, washed with saturated sodium hydrogencarbonate aqueous solution and water successively, dried over sodium sulfate anhydride, and concentrated. Concentrated hydrochloric acid (7.5 ml) was added to a solution containing the residue (5.53 g) in ethanol (30 ml). After being stirred for 3 hours at 90° C., the reaction mixture was neutralized with 5N sodium hydroxide aqueous solution (18 ml) and concentrated. The residue, with ethyl acetate added thereto, was washed with water and saturated brine successively, dried over sodium sulfate anhydride, and concentrated. The residue (4.33 g) was purified by silica gel column chromatography (silica gel 50 g, chloroform:methanol=10:1), thereby yielding the entitled compound (4.21 g) as pink wax.

Workup

  1. temperaturewhile being cooled with ice
  2. washwashed with saturated sodium hydrogencarbonate aqueous solution and water successively
  3. dry with materialdried over sodium sulfate anhydride
  4. concentrationconcentrated
  5. additionConcentrated hydrochloric acid (7.5 ml) was added to a solution
  6. additioncontaining the residue (5.53 g) in ethanol (30 ml)
  7. stirringAfter being stirred for 3 hours at 90° C.
  8. concentrationconcentrated
  9. additionThe residue, with ethyl acetate added
  10. washwas washed with water and saturated brine successively
  11. dry with materialdried over sodium sulfate anhydride
  12. concentrationconcentrated
  13. customThe residue (4.33 g) was purified by silica gel column chromatography (silica gel 50 g, chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-0e9887e2adfa44f9b41a147a919fd199
Source dataset
uspto-grants-2001_03
Patent number
US06204264B1

Reaction notes

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