Hydrochloric Acid → HCID 45381113, compound

HRID 1615006Notes

Reaction equation

HRID 1615006 reaction equation
[CH:1]1[C:13]2[N:12]([CH2:14][CH2:15][N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Al+3].[Cl-:22].[Cl-].[Cl-].[Cl:25][CH2:26][CH2:27][C:28](Cl)=[O:29].Cl>[N+](C1C=CC=CC=1)([O-])=O>[ClH:25].[CH2:17]([N:16]([CH2:19][CH3:20])[CH2:15][CH2:14][N:12]1[C:11]2[CH:10]=[CH:9][C:8]([C:28](=[O:29])[CH2:27][CH2:26][Cl:25])=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[C:3]([C:28](=[O:29])[CH2:27][CH2:26][Cl:22])[CH:4]=2)[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 693643-Chloropropionyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 58544901HCID 58544901, compound

Product 1

HCID 45381113HCID 45381113, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

A solution of compound 32 (17.9 g, 67.3 mmol) in nitrobenzene (150 mL) was cooled in an ice bath. AlCl3 (45.0 g, 337.1 mmol) was added in portions. Then 3-chloropropionyl chloride (32.4 mL, 336.7 mmol) was added dropwise for 10 min. The reaction mixture was stirred for 40 min (LC/MS monitoring), poured into a mixture of ice with diluted HCl, and extracted with CHCl3. The extract was evaporated. The residue was purified by chromatography in a thick short column (silica gel, CHCl3/MeOH 99:1→90:10) to afford 22.9 g (76.3%) of the hydrochloride 33.

Workup

  1. extractionextracted with CHCl3
  2. customThe extract was evaporated
  3. customThe residue was purified by chromatography in a thick short column (silica gel, CHCl3/MeOH 99:1→90:10)

Sources & evidence

ORD record
ord-b1390a1a2e054ee7bf4ceb8198c2077b
Source dataset
uspto-grants-2014_07
Patent number
US08765738B2

Reaction notes

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