Triethylamine → 4-(4-chloro-phenyl)-7,8-dimethoxy-4H-1,3,4-triaza-phenalene

HRID 1351223Notes

Reaction equation

HRID 1351223 reaction equation
[CH3:1][O:2][C:3]1[C:14]([O:15][CH3:16])=[CH:13][C:12]2=[C:17]3[C:4]=1[CH2:5][CH:6](O)[N:7]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)[C:8]3=[N:9][CH:10]=[N:11]2.C(N(CC)CC)C.CS(Cl)(=O)=O>ClCCl>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([N:7]2[CH:6]=[CH:5][C:4]3[C:17]4[C:8]2=[N:9][CH:10]=[N:11][C:12]=4[CH:13]=[C:14]([O:15][CH3:16])[C:3]=3[O:2][CH3:1])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 210984057,8-dimethoxy-4-(4-chloro-phenyl)-5,6-dihydro-4H-1,3,4-triaza-phenalen-5-ol

Product 1

HCID 117721594-(4-chloro-phenyl)-7,8-dimethoxy-4H-1,3,4-triaza-phenalene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7,8-dimethoxy-4-(4-chloro-phenyl)-5,6-dihydro-4H-1,3,4-triaza-phenalen-5-ol (140 mg, 0.39 mmol) (from Example 21, Step A, supra) and triethylamine (0.32 mL, 2.33 mmol) in dichloromethane (50 mL) at 0° C. was added methanesulfonyl chloride (0.12 mL, 1.55 mmol) (Aldrich). The reaction solution was the stirred at room temperature for 2 hours. The solution was then concentrated, the residue was purified by chromatography using EtOAc/CH2Cl2/NEt3 (1:1:0.01) as eluent to give the desired 4-(4-chloro-phenyl)-7,8-dimethoxy-4H-1,3,4-triaza-phenalene as a yellow solid. (Yield 47 mg, 55%).

Workup

  1. concentrationThe solution was then concentrated
  2. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-284bfd0f28634ab8b060fe60adf3f5b2
Source dataset
uspto-grants-2007_05
Patent number
US07217717B2

Reaction notes

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