Acetic Acid → HCID 178502014, compound

HRID 437796Notes

Reaction equation

HRID 437796 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:13]3[CH:14]=[C:15]([NH2:20])[C:16]([NH2:19])=[CH:17][CH:18]=3)[O:12][CH2:11][CH2:10][O:9]2)=[CH:4][CH:3]=1.[CH3:21][O:22][C:23]([NH:25][C:26](=NC(=O)OC)SC)=[O:24].C(O)(=O)C>ClC(Cl)Cl>[CH3:21][O:22][C:23](=[O:24])[NH:25][C:26]1[NH:19][C:16]2[CH:17]=[CH:18][C:13]([C:8]3([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[O:9][CH2:10][CH2:11][O:12]3)=[CH:14][C:15]=2[N:20]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 98708Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamateHCID 64548874-(2-(4-Fluorophenyl)-1,3-dioxolan-2-yl)benzene-1,2-diamine

Product 1

HCID 178502014HCID 178502014, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 5.5 parts of 4-[2-(4-fluorophenyl)-1,3-dioxolan2-yl]-1,2-benzenediamine, 6.2 parts of methyl [(methoxycarbonylamino)(methylthio)methylene]carbamate, 4.8 parts of acetic acid and 225 parts of trichloromethane is stirred and refluxed for 17 hours. The reaction mixture is evaporated in vacuo. The residue is triturated in methanol. The product is filtered off, washed with 2,2' -oxybispropane and dried, yielding 3 parts (42%) of methyl{ 5-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]-1H-benzimidazol-2-yl}carbamate; mp. 227.7° C.

Workup

  1. temperaturerefluxed for 17 hours
  2. customThe reaction mixture is evaporated in vacuo
  3. customThe residue is triturated in methanol
  4. filtrationThe product is filtered off
  5. washwashed with 2,2' -oxybispropane
  6. customdried

Sources & evidence

ORD record
ord-ebe53c538602438484bd819ffa199270
Source dataset
uspto-grants-1977_06
Patent number
US04032536

Reaction notes

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