Triethylamine → HCID 54534804, compound

HRID 1289351Notes

Reaction equation

HRID 1289351 reaction equation
[C:1]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14](=[O:18])[CH2:15][C:16]#[N:17])[CH:8]=1)(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([N:29]=[C:30](Cl)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)(=[O:28])=[O:27])=[CH:22][CH:21]=1.C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14](=[O:18])[C:15](=[C:30]([NH:29][S:26]([C:23]2[CH:22]=[CH:21][C:20]([CH3:19])=[CH:25][CH:24]=2)(=[O:28])=[O:27])[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:16]#[N:17])[CH:8]=1)(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3780018N-(4-Methylbenzene-1-sulfonyl)benzenecarboximidoyl chlorideHCID 21829783HCID 21829783, compound

Product 1

HCID 54534804HCID 54534804, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 4.89 g (20 mmol) of 3-(2-cyanoacetamido)phenyl methacrylate, 5.88 g (20 mmol) of N-(4-methylphenylsulfonyl)benzenecarboximidoyl chloride and 200 ml of methylene chloride was added dropwise 4.05 g (40 mmol) of triethylamine with 10 ml of methylene chloride rinse. The resultant solution was stirred for 1 hr and washed twice with 10% HCl and once with water. The solution was dried over magnesium sulfate and concentrated after adding t-butylpyrocatechol inhibitor. The solid residue was treated with ligroine, collected and recrystallized from ethanol.

Workup

  1. washrinse
  2. washwashed twice with 10% HCl and once with water
  3. dry with materialThe solution was dried over magnesium sulfate
  4. concentrationconcentrated
  5. additionafter adding t-butylpyrocatechol inhibitor
  6. additionThe solid residue was treated with ligroine
  7. customcollected
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-d23397f4bb074e48a0743d223f0761eb
Source dataset
uspto-grants-1998_05
Patent number
US05750305

Reaction notes

Loading…