Stearoyl chloride → HCID 22013765, compound

HRID 1532691Notes

Reaction equation

HRID 1532691 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][N:22]([CH3:24])[CH3:23])[C:12]([NH:14][CH3:15])=[O:13].[C:25](Cl)(=O)[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][CH2:40][CH2:41][CH3:42]>C(Cl)(Cl)Cl>[CH3:24][N:22]([CH3:23])[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:42]1[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][CH2:26][CH3:25]

Participants

5

Reactant 3

HCID 8212Stearoyl chlorideHCID 8471TriethylamineHCID 22013776HCID 22013776, compound

Product 1

HCID 22013765HCID 22013765, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Triethylamine (1.00 ml) was added to a solution containing 3-amino-4-{[2-(dimethylamino)ethyl]amino}-N-methylbenzamide (1.500 g) in chloroform (15 ml), and then stearoyl chloride (2.20 mnl) was added thereto while being cooled with ice. After being stirred for 2.5 hours, the reaction mixture was diluted with chloroform, washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and concentrated. Concentrated hydrochloric acid (5.3 ml) was added to a solution containing the residue (3.030 g) in ethanol (30 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 1N sodium hydroxide aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and concentrated. The residue (3.737 g) was purified by silica gel column chromatography (silica gel 75 g, chloroform:methanol=50:1-30:1), thereby yielding the entitled compound (2.225 g) as pale yellow solid.

Workup

  1. temperaturewhile being cooled with ice
  2. washwashed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively
  3. dry with materialdried over sodium sulfate anhydride
  4. concentrationconcentrated
  5. additionConcentrated hydrochloric acid (5.3 ml) was added to a solution
  6. additioncontaining the residue (3.030 g) in ethanol (30 ml)
  7. stirringAfter being stirred for 1.5 hours at 90° C.
  8. concentrationthe reaction mixture was concentrated
  9. additionThe residue, with ethyl acetate added
  10. washwas washed with 1N sodium hydroxide aqueous solution and saturated brine successively
  11. dry with materialdried over sodium sulfate anhydride
  12. concentrationconcentrated
  13. customThe residue (3.737 g) was purified by silica gel column chromatography (silica gel 75 g, chloroform:methanol=50:1-30:1)

Sources & evidence

ORD record
ord-1dc2d949e0cb40f0b9def840ea84f18c
Source dataset
uspto-grants-2001_03
Patent number
US06204264B1

Reaction notes

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