Sulfur → HCID 15037356, compound

HRID 1460522Notes

Reaction equation

HRID 1460522 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][CH:12]1[CH2:18][CH2:17][CH2:16][N:15]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:14][CH2:13]1)=S.[S]>[Hg]=O.O1CCCC1>[NH:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:9]1[NH:11][CH:12]1[CH2:18][CH2:17][CH2:16][N:15]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 5362487SulfurHCID 15037318HCID 15037318, compound

Product 1

HCID 15037356HCID 15037356, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 30856Mercuric oxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 33.6 parts of ethyl 4-[[[(2-aminophenyl)amino]thioxomethyl]amino]hexahydro-1H-azepine-1-carboxylate, 26 parts of mercury(II) oxide, 0.1 parts of sulfur and 450 parts of tetrahydrofuran was stirred for 3 hours at reflux temperature. The reaction mixture was filtered while hot over diatomaceous earth and the filtrate was evaporated. The residue was boiled in acetonitrile. The product was filtered off and dried, yielding 24.5 parts (81.0%) of ethyl 4-(1H-benzimidazol-2-ylamino)hexahydro-1H-azepine-1-carboxylate; mp. 174.6° C. (compound 10).

Workup

  1. temperatureat reflux temperature
  2. filtrationThe reaction mixture was filtered while hot over diatomaceous earth
  3. customthe filtrate was evaporated
  4. filtrationThe product was filtered off
  5. customdried

Sources & evidence

ORD record
ord-50a0287e95f54a209df5de6348181225
Source dataset
uspto-grants-1991_12
Patent number
US05071846

Reaction notes

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