p-Anisoyl chloride → HCID 59736803, compound

HRID 252830Notes

Reaction equation

HRID 252830 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:11]2[N:12]=[C:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[S:14][CH:15]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH3:24][O:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH3:24][O:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([NH:1][C:2]2[CH:3]=[C:4]([C:11]3[N:12]=[C:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])[S:14][CH:15]=3)[CH:5]=[CH:6][C:7]=2[N+:8]([O-:10])=[O:9])=[O:31])=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 7477p-Anisoyl chlorideHCID 59736955HCID 59736955, compound

Product 1

HCID 59736803HCID 59736803, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of compound 150 (390 mg, 1.28 mmol) in pyridine was added 4-methoxybenzoyl chloride (181 mg, 1.06 mmol) and 4-(N,N-dimethylamino)pyridine (13 mg, 0.11 mmol). The mixture was stirred for 16 h and partitioned between EtOAc and H2O. The organic layer was washed with brine and some compound was collected by filtration. The filtrate was dried over MgSO4, filtered and concentrated in vacuo and then crystallized from a mixture of EtOAc/Hexanes. The two crops were combined affording the title compound 151 (358 mg, 72% yield). 1H NMR: (400 MHz, CD3OD) δ(ppm): 11.73 (s, 1H), 10.71 (s, 1H), 8.36 (d, J=2.0 Hz, 1H), 8.08 (d, J=8.6 Hz, 1H), 7.95 (d, J=9.0 Hz, 2H), 7.86 (d, J=0.8 Hz, 1H), 7.83 (dd, J=8.6, 2.0 Hz, 1H), 7.10 (d, J=9.0 Hz, 2H), 3.85 (s, 3H), 1.50 (s, 9H).

Workup

  1. custompartitioned between EtOAc and H2O
  2. washThe organic layer was washed with brine
  3. filtrationsome compound was collected by filtration
  4. dry with materialThe filtrate was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customcrystallized from a mixture of EtOAc/Hexanes

Sources & evidence

ORD record
ord-a156ca2119ac4ffeb4d88f3bcee3be12
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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