Thiocarbonyl diimidazole → HCID 136014677, compound

HRID 1427320Notes

Reaction equation

HRID 1427320 reaction equation
Cl.Cl.[N:3]1[NH:4][N:5]=[N:6][C:7]=1[C:8]1[CH:9]=[C:10]([NH2:15])[C:11]([NH2:14])=[CH:12][CH:13]=1.[C:16](C1NC=CN=1)(C1NC=CN=1)=[S:17]>C(#N)C>[N:6]1[NH:5][N:4]=[N:3][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]2[NH:14][C:16](=[S:17])[NH:15][C:10]=2[CH:9]=1

Participants

4

Reactant 2

HCID 11412697Thiocarbonyl diimidazoleHCID 67299086HCID 67299086, compound

Product 1

HCID 136014677HCID 136014677, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To 4-(2H-tetrazol-5-yl)-benzene-1,2-diamine dihydrochloride (6.40 g, 25 mmol) in acetonitrile (100 ml) was added thiocarbonyl di-imidazole (4.86 g, 28 mmol). A further 100 ml of acetonitrile was added. The reaction was then stirred for 5 hours and the reaction analyzed by HPLC. The solvent was removed under reduced pressure and water added (100 ml). The pH of the reaction mixture was adjusted to pH 2.0 and the solid filtered and washed with water (50 ml). The material was dried to give 5-(2H-tetrazol-5-yl)-1,3-dihydrobenzimidazole-2-thione (3.35 g, 61% yield). The material was suspended in water (300 ml) and the pH adjusted to 11.0 with 40% (v/v) NaOH. Methanol (15 ml) was then added followed by Activated carbon (0.38 g) and the mixture stirred for 1 hour. The mixture was filtered and the solvent removed, under reduced pressure, to half its volume. The pH was adjusted to 2.0 with 50% (v/v) hydrochloric acid to yield an off white solid. The solid was filtered off and washed with water. The purity was >98% by hplc Rt=7.8 mins. The material was dried to yield 5-(2H-tetrazol-5-yl)-1,3-dihydrobenzimidazole-2-thione (2.37 g). 1H NMR (d6-DMSO, 400 MHz) 12.88 ppm (1H, s), 12.84 ppm (1H, s), 7.82 ppm (1H, dd, 8.4 Hz, 1.6 Hz), 7.78 ppm (1H, m), 7.30 ppm (1H, d, 8 Hz). MS (high resolution EI). Found 218.036514 m/z C8H6N6S to +4 ppm mass accuracy.

Workup

  1. customThe solvent was removed under reduced pressure and water
  2. additionadded (100 ml)
  3. filtrationthe solid filtered
  4. washwashed with water (50 ml)
  5. customThe material was dried

Sources & evidence

ORD record
ord-b43c5dbb95064060b3a12f94a6079c5a
Source dataset
uspto-grants-2015_01
Patent number
US08933206B2

Reaction notes

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