Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamate → HCID 178502055, compound

HRID 241078Notes

Reaction equation

HRID 241078 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([N+:9]([O-])=O)=[CH:4][N:3]=1.[CH3:12][O:13][C:14]([NH:16][C:17](=NC(OC)=O)SC)=[O:15]>C(O)(=O)C.[Fe]>[Br:1][C:2]1[N:3]=[CH:4][C:5]2[N:9]=[C:17]([NH:16][C:14](=[O:15])[O:13][CH3:12])[NH:8][C:6]=2[CH:7]=1

Participants

5

Reactant 2

HCID 98708Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamateHCID 130404032-Bromo-5-nitropyridin-4-amine

Product 1

HCID 178502055HCID 178502055, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×

Conditions

Temperature
75 °C

Procedure

A solution of 2-bromo-5-nitropyridin-4-amine (1.5 g, 6.9 mmol) in acetic acid (20 mL) was added in portions into a 75° C. suspension of iron powder (1.5 g, 27 mmol) in acetic acid (20 mL). The reaction mixture was stirred at 75° C. for 2 h, cooled to room temperature, and filtered through celite. To the filtrate was added 1,3-bis(methoxycarbonyl)-2-methyl-2-thiopseudourea (1.4 g, 6.9 mmol), and the mixture was stirred at 65° C. for 60 h. The reaction mixture was cooled to room temperature and concentrated. The solid residue was triturated with dichloromethane and dried to give the title Compound (1.8 g, quantitative yield) as an orange solid. MS (EI) for C8H7BrN4O2: 271/273 (MH+).

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered through celite
  3. stirringthe mixture was stirred at 65° C. for 60 h
  4. temperatureThe reaction mixture was cooled to room temperature
  5. concentrationconcentrated
  6. customThe solid residue was triturated with dichloromethane
  7. customdried

Sources & evidence

ORD record
ord-39976cfa02004c179b06b915b17810f5
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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