Triethylamine → HCID 178483985, compound

HRID 2236707Notes

Reaction equation

HRID 2236707 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]([CH3:31])[CH2:19][CH2:20][S:21]([C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=1)(=[O:23])=[O:22].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:30][C:27]1[CH:26]=[CH:25][C:24]([S:21]([CH2:20][CH2:19][N:18]([CH3:31])[CH3:17])(=[O:23])=[O:22])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 203368214-((2-(Dimethylamino)ethyl)sulfonyl)anilineHCID 68692760(E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

Product 1

HCID 178483985HCID 178483985, compoundYield 37.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(4E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (0.17 g, 0.61 mmol) and 4-(2-dimethylamino-ethanesulfonyl)-phenylamine (0.14 g, 0.61 mmol) were stirred in N,N-dimethylformamide (3 mL) and triethylamine (0.16 mL) at 60-70° C. 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]sulfonyl}-phenyl)amino]methylene}isoquinoline-1,3(2H,4H)-dione (0.11 g, 36%) as a golden powder.

Workup

  1. customat 60-70° C
  2. customThe reaction mixture is quenched by the addition of water
  3. customThe solid material is then collected
  4. washwashed with diethyl ether, water, and methanol
  5. customdried under vacuum

Sources & evidence

ORD record
ord-2c09cb639fc94ee9905e2d9ad94fe660
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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