1,3-DI-Boc-2-methylisothiourea → HCID 178452970, compound

HRID 1823769Notes

Reaction equation

HRID 1823769 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[NH2:8].[C:10]([O:14][C:15]([NH:17][C:18](=NC(OC(C)(C)C)=O)SC)=[O:16])([CH3:13])([CH3:12])[CH3:11]>CO.C(O)(=O)C>[C:10]([O:14][C:15](=[O:16])[NH:17][C:18]1[NH:8][C:7]2[CH:6]=[CH:5][C:4]([OH:9])=[CH:3][C:2]=2[N:1]=1)([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 2

HCID 5466031,3-DI-Boc-2-methylisothioureaHCID 27729703,4-Diaminophenol

Product 1

HCID 178452970HCID 178452970, compoundYield 61.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

5.75 g of 3,4-diaminophenol were combined with 15.5 g of 1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea in 150 ml methanol and 22 ml acetic acid in a round bottom flask. The reaction mixture was heated to reflux with stirring for 3 hours. Solvents were then evaporated under reduce pressure yielding 7.13 g crude (5-hydroxy-1H-benzoimidazol-2-yl)-carbamic acid tert-butyl ester.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. customSolvents were then evaporated

Sources & evidence

ORD record
ord-fcff09dbfa11479f8d5c4d77baad3a1d
Source dataset
uspto-grants-2006_05
Patent number
US07041668B2

Reaction notes

Loading…