tert-butyl N-[(4-aminophenyl)methyl]carbamate → HCID 22981319, compound

HRID 1861914Notes

Reaction equation

HRID 1861914 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].I.[CH:18]1([NH:21][C:22](=[NH:25])SC)[CH2:20][CH2:19]1>N1C=CC=CC=1>[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:22]([NH2:25])=[N:21][CH:18]2[CH2:20][CH2:19]2)=[CH:13][CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2756041tert-butyl N-[(4-aminophenyl)methyl]carbamateHCID 178503964HCID 178503964, compound

Product 1

HCID 22981319HCID 22981319, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The compound (0.946 g) obtained in Example 82 was added to a mixture of N-cyclopropyl-S-methylisothiourea hydroiodide (1.0 g) and pyridine (10 ml) and heated under reflux for 2 days. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=2:1) to give 0.131 g of the titled compound (yield, 12%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 days
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-b636903c675b4450b91810c9334e62d5
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

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