Diisopropylamine → HCID 23370104, compound

HRID 1901049Notes

Reaction equation

HRID 1901049 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:25])[C:10]1[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:13]([OH:20])=[C:12]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:11]=1.C(NC(C)C)(C)C.Cl[C:34]([O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:35]>ClCCl>[C:21]([C:12]1[CH:11]=[C:10]([CH:15]=[C:14]([C:16]([CH3:18])([CH3:19])[CH3:17])[C:13]=1[OH:20])[C:9]([NH:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:34](=[O:35])[O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:25])([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 15891Phenyl chloroformateHCID 23370116N-(2-aminophenyl)-3,5-di-t-butyl-4-hydroxybenzamide

Product 1

HCID 23370104HCID 23370104, compoundYield 1,095.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-(2-aminophenyl)-3,5-di-t-butyl-4-hydroxybenzamide (0.85 g) and diisopropylamine (0.39 ml) were suspended in dichloromethane (20 ml) and a solution of phenyl chloroformate (16.8 g) in dichloromethane (30 ml) was added dropwise under ice-cooling. After stirring the mixture overnight, the reaction solution was washed with water, saturated saline, dried over anhydrous MgSO4 and the solvent was distilled off. Purification of the residue by a silica gel column chromatography (chloroform:ethyl acetate=10:1) followed by crystallization from hexane/ethyl acetate afforded phenyl N-[2-(3,5-di-t-butyl-4-hydroxybenzoylamino)phenyl]carbamate (12.6 g, 49%).

Workup

  1. temperaturecooling
  2. washthe reaction solution was washed with water, saturated saline
  3. dry with materialdried over anhydrous MgSO4
  4. distillationthe solvent was distilled off
  5. customPurification of the residue by a silica gel column chromatography (chloroform:ethyl acetate=10:1)
  6. customfollowed by crystallization from hexane/ethyl acetate

Sources & evidence

ORD record
ord-4e8c09844fd24b25af4c01a57dab1cc3
Source dataset
uspto-grants-1996_11
Patent number
US05576335

Reaction notes

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