Benzoyl chloride → HCID 15034984, compound

HRID 1090226Notes

Reaction equation

HRID 1090226 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][NH:9][C:10]2[C:18]3[CH:19]=[CH:20][CH:21]=[C:16]4[C:17]=3[C:12](=[CH:13][CH:14]=[CH:15]4)[N:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.Cl.Cl.N1(CCCNC2C3C=CC=C4C=3C(=CC=C4)N=2)C=CN=C1.[C:45](Cl)(=[O:52])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[N:11]1[C:12]2[C:17]3[C:16](=[CH:21][CH:20]=[CH:19][C:18]=3[C:10]=1[N:9]([CH2:8][CH2:7][CH2:6][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)[C:45](=[O:52])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[CH:15]=[CH:14][CH:13]=2

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 178419797HCID 178419797, compoundHCID 178478518HCID 178478518, compound

Product 1

HCID 15034984HCID 15034984, compoundYield 14.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Five grams of N-(3-(1H-imidazol-l-yl)propyl)benz(cd)indole-2-amine (the free base of the compound of Example 1) and 100 mg of 4-dimethylaminopyridine were dissolved in 50 ml of pyridine. The solution was stirred as 2.8 grams of benzoyl chloride was slowly added. An exotherm was noted. The mixture was stirred at room temperature for 4 hours and then drowned onto 500 ml of ice. The precipitated solid was collected, washed with water, and dried. Recrystallization from chloroform-hexane gave 1.0 gram of desired compound, mp 148° C.-153° C., with decomposition.

Workup

  1. additionwas slowly added
  2. customThe precipitated solid was collected
  3. washwashed with water
  4. customdried
  5. customRecrystallization from chloroform-hexane

Sources & evidence

ORD record
ord-d9d9a10696f64c88857b29c0ff63cad2
Source dataset
uspto-grants-1992_01
Patent number
US05081131

Reaction notes

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