Diethylcarbamoyl chloride → HCID 178464342, compound

HRID 2236615Notes

Reaction equation

HRID 2236615 reaction equation
[I: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:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([OH:25])[CH:18]=1.[CH2:26]([N:28]([CH2:32][CH3:33])[C:29](Cl)=[O:30])[CH3:27].C(N(CC)CC)C>CN(C=O)C.N1C=CC=CC=1>[CH2:26]([N:28]([CH2:32][CH3:33])[C:29](=[O:30])[O:25][C:19]1[CH:18]=[C:17]([CH2:16][NH:15]/[CH:14]=[C:5]2\[C:6](=[O:13])[NH:7][C:8](=[O:12])[C:9]3[C:4]\2=[CH:3][C:2]([I:1])=[CH:11][CH:10]=3)[CH:22]=[CH:21][C:20]=1[O:23][CH3:24])[CH3:27]

Participants

6

Reactant 3

HCID 6916Diethylcarbamoyl chlorideHCID 8471TriethylamineHCID 178491081HCID 178491081, compound

Product 1

HCID 178464342HCID 178464342, compoundYield 56.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (4Z)-6-iodo-4-{[(3-hydroxy-4-methoxybenzyl)amino]methylene}isoquinoline-1,3(2H,4H)-dione (0.30 g, 0.67 mmol) in 3 mL of N,N′-dimethylformamide and 2 mL of pyridine is added diethylcarbamylchloride (0.10 mL, 0.80 mmol) and 0.21 mL (2.00 mmol) of triethylamine. The reaction mixture is stirred at 80° C. for 4 h and then at room temperature over weekend under N2. Mass spectroscopy suggested the completion of reaction. The reaction mixture is concentrated, and 2 mL of MeOH is added to break up the solid, followed by addition of excess amount of Et2O. The precipitate is filtered, washed successively with water, methanol, ether and hexane, and dried in oven (60° C.) overnight to afford 0.207 g (56.6% yield) of tan solid: mp 128-130° C.; MS (ESI) m/z 548.2 (M−H)−1

Workup

  1. waitat room temperature over weekend under N2
  2. customthe completion of reaction
  3. concentrationThe reaction mixture is concentrated
  4. addition2 mL of MeOH is added
  5. additionfollowed by addition of excess amount of Et2O
  6. filtrationThe precipitate is filtered
  7. washwashed successively with water, methanol, ether and hexane
  8. customdried in oven (60° C.) overnight

Sources & evidence

ORD record
ord-ee233f9ee9db41fc98bfc1c519f5f039
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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