Stearoyl chloride → HCID 9871822, compound

HRID 1532664Notes

Reaction equation

HRID 1532664 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=1[NH:19][CH2:20][CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])[C:12]([NH:14][CH3:15])=[O:13].[C:26](Cl)(=O)[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][CH2:40][CH2:41][CH2:42][CH3:43]>C(Cl)(Cl)Cl>[CH3:24][N:23]([CH3:25])[CH2:22][CH2:21][CH2:20][N:19]1[C:18]2[CH:17]=[CH:16][C:11]([C:12]([NH:14][CH3:15])=[O:13])=[CH:10][C:9]=2[N:8]=[C:43]1[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][CH2:27][CH3:26]

Participants

5

Reactant 3

HCID 8212Stearoyl chlorideHCID 8471TriethylamineHCID 220137513-Amino-4-[[3-(dimethylamino)propyl]amino]-N-methylbenzamide

Product 1

HCID 9871822HCID 9871822, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Triethylamine (0.77 ml) was added to a solution containing 3-amino-4-{[3-(dimethylamino)propyl]amino}-N-methylbenzamide (1.44 g) in chloroform (10 ml), and then a solution containing stearoyl chloride (1.51 g) in chloroform (5 ml) was added thereto while being cooled with ice. After being stirred for 1.5 hours at room temperature, the reaction mixture was diluted with chlorofonr, washed with saturated sodium hydrogencarbonate aqueous solution and water successively, dried over sodium sulfate anhydride, and concentrated. Concentrated hydrochloric acid (4.00 ml) was added to a solution containing the residue (2.78 g) in ethanol (25 ml). After being stirred for 1.5 hours at 90° C., the reaction mixture was concentrated. The residue, with ethyl acetate added thereto, was washed with 4N sodium hydroxide aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and concentrated. The residue (2.77 g) was purified by silica gel column chromatography (silica gel 50 g, chloroform:methanol=50:1-10:1), thereby yielding the entitled compound (2.11 g) as grayish yellow solid.

Workup

  1. additionwas added
  2. temperaturewhile being cooled with ice
  3. additionthe reaction mixture was diluted with chlorofonr
  4. washwashed with saturated sodium hydrogencarbonate aqueous solution and water successively
  5. dry with materialdried over sodium sulfate anhydride
  6. concentrationconcentrated
  7. additionConcentrated hydrochloric acid (4.00 ml) was added to a solution
  8. additioncontaining the residue (2.78 g) in ethanol (25 ml)
  9. stirringAfter being stirred for 1.5 hours at 90° C.
  10. concentrationthe reaction mixture was concentrated
  11. additionThe residue, with ethyl acetate added
  12. washwas washed with 4N sodium hydroxide aqueous solution and saturated brine successively
  13. dry with materialdried over sodium sulfate anhydride
  14. concentrationconcentrated
  15. customThe residue (2.77 g) was purified by silica gel column chromatography (silica gel 50 g, chloroform:methanol=50:1-10:1)

Sources & evidence

ORD record
ord-695e53c7227246ce9483aedf4ad050a3
Source dataset
uspto-grants-2001_03
Patent number
US06204264B1

Reaction notes

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