Methanol → NSC154754

HRID 473833Notes

Reaction equation

HRID 473833 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.COCCOC.CO.[CH3:18][O:19][C:20]([NH:22][C:23](=NC(OC)=O)SC)=[O:21]>C(OCC)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]=[C:23]([NH:22][C:20](=[O:21])[O:19][CH3:18])[NH:9][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 80711,2-DimethoxyethaneHCID 98708Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamateHCID 3235934-Bromobenzene-1,2-diamine

Product 1

HCID 290654NSC154754Yield 77.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
105 °C

Procedure

To a slurry of 4-bromobenzene-1,2-diamine (2.1 g, 11 mmol), 1,2-dimethoxyethane (20 mL) and methanol (5 mL) was added 1,3-bis(methoxycarbonyl)-2-methyl-2-thiopseudourea (4.0 g, 19 mmol). The reaction mixture was heated (105° C.) for 12 h and then diluted with ethyl ether (100 mL). The resulting precipitate was collected by filtration and rinsed with ethyl ether (2×25 mL) to provide methyl 6-bromo-1H-benzo[d]imidazol-2-ylcarbamate (2.3 g, 77% yield). MS (EI) for C9H8BrN3O2: 271 (MH+).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washrinsed with ethyl ether (2×25 mL)

Sources & evidence

ORD record
ord-78286d968da94b96a4191904bb91bcd0
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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