P-Phenylenediamine → HCID 86757195, compound

HRID 1386827Notes

Reaction equation

HRID 1386827 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([NH2:8])[CH:2]=1.[C:9]([NH:16][CH2:17][C:18]([OH:20])=O)([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C1([N:27]=C=NC2CCCCC2)CCCCC1>O1CCCC1>[C:12]([O:11][C:9]([NH:16][CH2:17][C:18]([NH:27][NH:7][C:6]1[CH:5]=[CH:4][C:3]([NH2:8])=[CH:2][CH:1]=1)=[O:20])=[O:10])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 7814P-PhenylenediamineHCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycine

Product 1

HCID 86757195HCID 86757195, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8.65 g (0.08 mol) of p-phenylenediamine are dissolved in 300 ml of absolute tetrahydrofuran (THF) together with 15.3 g (0.088 mol) of N-Boc-glycine, and 18.05g (0.088 mol) of dicyclohexylcarbodiimide is added in portions. After 5 h, the deposited precipitate is filtered off with suction, the filtrate is concentrated, and the product is purified by chromatography on silica gel by means of ethyl acetate/methanol/acetic acid and then crystallized from ethyl acetate/petroleum ether. The yield of the process was 13.5 g with a melting point 144° C.

Workup

  1. additionis added in portions
  2. filtrationthe deposited precipitate is filtered off with suction
  3. concentrationthe filtrate is concentrated
  4. customthe product is purified by chromatography on silica gel by means of ethyl acetate/methanol/acetic acid
  5. customcrystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-7392d49a88004b37a80f8afeffdd5de7
Source dataset
uspto-grants-2001_07
Patent number
US06265588B1

Reaction notes

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