Hydrochloric Acid → [(2,4,6-Triisopropyl-phenyl)-acetyl]-sulfamic acid 4-(aminomethylene)-2,6-diisopropyl-phenyl ester

HRID 2289690Notes

Reaction equation

HRID 2289690 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH:9]([CH3:11])[CH3:10])[C:6]([O:12][S:13](=[O:34])(=[O:33])[NH:14][C:15](=[O:32])[CH2:16][C:17]2[C:22]([CH:23]([CH3:25])[CH3:24])=[CH:21][C:20]([CH:26]([CH3:28])[CH3:27])=[CH:19][C:18]=2[CH:29]([CH3:31])[CH3:30])=[C:5]([CH:35]([CH3:37])[CH3:36])[CH:4]=1)#[N:2].[H][H].Cl>N.C(OCC)C.[Ni]>[NH2:2][CH:1]=[C:3]1[CH:4]=[C:5]([CH:35]([CH3:36])[CH3:37])[C:6]([O:12][S:13](=[O:33])(=[O:34])[NH:14][C:15](=[O:32])[CH2:16][C:17]2[C:18]([CH:29]([CH3:30])[CH3:31])=[CH:19][C:20]([CH:26]([CH3:27])[CH3:28])=[CH:21][C:22]=2[CH:23]([CH3:25])[CH3:24])=[C:7]([CH:9]([CH3:11])[CH3:10])[CH2:8]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 10165237[(2,4,6-Triisopropyl-phenyl)-acetyl]-sulfamic acid 4-cyano-2,6-diisopropyl-phenyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 53945870[(2,4,6-Triisopropyl-phenyl)-acetyl]-sulfamic acid 4-(aminomethylene)-2,6-diisopropyl-phenyl ester

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 3283Diethyl EtherSolvent

Procedure

[(2,4,6-Triisopropyl-phenyl)-acetyl]-sulfamic acid 4-cyano-2,6-diisopropyl-phenyl ester (5.15 g, 9.8 mmol) was dissolved in 100 mL of methanolic ammonia and 2.0 g of Raney-nickel was added. The resulting mixture was stirred under 50 psi of hydrogen at room temperature for 20 hours. Filtered and concentrated the residue to give a dark solid. Suspended in diethyl ether and acidified with HCl gas. Concentrated in vacuo and neutralized the residue with saturated aqueous sodium bicarbonate. The resulting white suspension was used without further purification.

Workup

  1. filtrationFiltered
  2. concentrationconcentrated the residue
  3. customto give a dark solid
  4. concentrationConcentrated in vacuo
  5. customThe resulting white suspension was used without further purification

Sources & evidence

ORD record
ord-c536a0f073004c3ea1f33876b293bad1
Source dataset
uspto-grants-2000_07
Patent number
US06093744

Reaction notes

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