Pyridine → HCID 18403477, compound

HRID 1017211Notes

Reaction equation

HRID 1017211 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[CH3:22][O:23][CH2:24][C:25](Cl)=[O:26]>O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:25](=[O:26])[CH2:24][O:23][CH3:22])=[CH:13][CH:14]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 1049PyridineHCID 96623Methoxyacetyl chlorideHCID 688611tert-Butyl (4-aminophenyl)carbamate

Product 1

HCID 18403477HCID 18403477, compoundYield 104%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of N-t-butoxycarbonyl-1,4-phenylene diamine (0.25 g) in dry tetrahydrofuran (20 ml) were added pyridine (0.12 ml) and methoxyacetyl chloride (0.15 g) and the reaction mixture was stirred for 1 hrs. The solution was diluted with ethyl acetate (50 ml), washed with a 3N solution of hydrochloric acid (30 ml) and brine (30 ml), dried and concentrated in vacuum to give the title compound (0.35 g). T.l.c. CH/EA acetate 1/1. Rf=0.33.

Workup

  1. washwashed with a 3N solution of hydrochloric acid (30 ml) and brine (30 ml)
  2. customdried
  3. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-3552ef8fec234076b775962714cd96d5
Source dataset
uspto-grants-2002_11
Patent number
US06479488B1

Reaction notes

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