N,N-Diethylaniline → HCID 57764516, compound

HRID 402312Notes

Reaction equation

HRID 402312 reaction equation
[C:1]([O:9][C@@H:10]1[C@H:14]([O:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([CH2:24][O:25][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:12][C@H:11]1[N:34]1[C:38]2=[CH:39][N:40]=[N:41][C:42](=O)[C:37]2=[N:36][CH2:35]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C1C=CC=CC=1)C.P(Cl)(Cl)[Cl:56]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[Cl:56][C:42]1[N:41]=[N:40][CH:39]=[C:38]2[N:34]([C@@H:11]3[O:12][C@H:13]([CH2:24][O:25][C:26](=[O:33])[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C@@H:14]([O:15][C:16](=[O:23])[C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C@H:10]3[O:9][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:35]=[N:36][C:37]=12

Participants

6

Reactant 3

HCID 7061N,N-DiethylanilineHCID 24387Phosphorus trichlorideHCID 86597447HCID 86597447, compound

Product 1

HCID 57764516HCID 57764516, compound

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution containing the compound from Step B (1.32 g, 2.27 mmol), the N,N-diethylaniline (365 μL), tetrabutylammonium chloride (1.2 g), freshly distilled phosphorus chloride (1.3 μL) and anhydrous acetonitrile (17 mL) was stirred at 90° C. for 1 hour. The reaction mixture was poured over cracked ice/water. The aqueous layer was extracted with dichloromethane (3×60 mL). The organic layer was washed with sodium hydrogenocarbonate 5%, water and was evaporated to dryness. The crude product was purified on silica gel using n-hexane/ethyl acetate (3/1) as eluant to give the title compound (404 mg) as a yellow powder.

Workup

  1. extractionThe aqueous layer was extracted with dichloromethane (3×60 mL)
  2. washThe organic layer was washed with sodium hydrogenocarbonate 5%, water
  3. customwas evaporated to dryness
  4. customThe crude product was purified on silica gel

Sources & evidence

ORD record
ord-ce1d2afd9c0040f6beb9a91a29901cf3
Source dataset
uspto-grants-2014_06
Patent number
US08742101B2

Reaction notes

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