Triethylamine → HCID 178483974, compound

HRID 2236690Notes

Reaction equation

HRID 2236690 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]/OC.[CH3:17][N:18]([CH3:29])[CH2:19][CH2:20][S:21][C:22]1[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=1.C(N(CC)CC)C>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]\[NH:28][C:25]1[CH:24]=[CH:23][C:22]([S:21][CH2:20][CH2:19][N:18]([CH3:29])[CH3:17])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 432994394-{[2-(Dimethylamino)ethyl]sulfanyl}anilineHCID 68692760(E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

Product 1

HCID 178483974HCID 178483974, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(4E)-6-Bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (0.21 g, 0.76 mmol) and 4-(2-dimethylamino-ethylsulfanyl)-phenylamine (0.15 g, 0.76 mmol) were stirred in N,N-dimethylformamide (5 mL) and triethylamine (0.3 mL) at 60-70° C. for 5 minutes and then at room temperature for 10 minutes. The reaction mixture is quenched by the addition of water. The solid material is then collected, washed with diethyl ether, water, and methanol, and then dried under vacuum to give (4Z)-6-bromo-4-{[(4-{[2-(dimethylamino)ethyl]thio}phenyl)amino]methylene}isoquinoline-1,3(2H,4H)-dione (0.22 mg, 65%) as a golden powder.

Workup

  1. customThe reaction mixture is quenched by the addition of water
  2. customThe solid material is then collected
  3. washwashed with diethyl ether, water, and methanol
  4. customdried under vacuum

Sources & evidence

ORD record
ord-821a714a3a614d2cb625109d52a93874
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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