Triethylamine → HCID 13034031, compound

HRID 1953136Notes

Reaction equation

HRID 1953136 reaction equation
[CH2:1]([NH:5][C:6]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[NH:10][C:9]1=[S:17])=[O:7])[CH2:2][CH2:3][CH3:4].BrBr.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:1]([N:5]1[C:6](=[O:7])[N:8]2[C:9](=[N:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=32)[S:17]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24408BromineHCID 13034028HCID 13034028, compound

Product 1

HCID 13034031HCID 13034031, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(butylcarbamoyl)-1,3-dihydrobenzimidazole-2-thione (39.89 g, 0.16 mole) in 250 mL of chloroform, was added 25.57 g (0.16 mole) of bromine, in 110 mL of chloroform, at 0° C. After the addition was complete, triethylamine (44.6 mL, 0.32 mole), in 80 mL of chloroform, was added dropwise to the reaction mixture. The mixture was stirred at 0° C for an additional 4 h, and then stirred at room temperature for 14 h. The resulting mixture was washed with water and then with a 10% sodium sulfate solution. The organic layer was dried over magnesium sulfate and evaporated to give the crude product. Recrystallization from methanol gave 27.10 g (69%) of 2-butyl-1,2,4-thiadiazolo[4,5-a]benzimidazole-3(2H)-one as colourless crystals: mp 153-154° C. (lit.: 156-157° C., Martin et al. Tetrahedron 1983, 39, 2311).

Workup

  1. customat 0° C
  2. additionAfter the addition
  3. stirringstirred at room temperature for 14 h
  4. washThe resulting mixture was washed with water
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customevaporated
  7. customto give the crude product
  8. customRecrystallization from methanol

Sources & evidence

ORD record
ord-c65f772f695d496bb027c98ee2cad344
Source dataset
uspto-grants-2000_09
Patent number
US06114537

Reaction notes

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