Butyl isocyanate → HCID 13034028, compound

HRID 2289588Notes

Reaction equation

HRID 2289588 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[CH2:11]([N:15]=[C:16]=[O:17])[CH2:12][CH2:13][CH3:14]>>[CH2:11]([NH:15][C:16]([N:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[NH:6][C:2]1=[S:1])=[O:17])[CH2:12][CH2:13][CH3:14]

Participants

3

Reactant 2

HCID 8110Butyl isocyanateHCID 178527775HCID 178527775, compound

Product 1

HCID 13034028HCID 13034028, compoundYield 89.4%

Conditions

Temperature
135 °C

Procedure

The mixture of 2-mercaptobenzimidazole (29.30 g, 0.195 mole) and butyl isocyanate (48.3 mL, 0.33 mole) in a 500 ml of round-bottom flask equipped with a condenser was heated to 130-140° C. in an oil bath for 45 min. After the reaction mixture was cooled to room temperature, the solid was filtered, washed with hexane, and dried under vacuum to give 43.48 g (89%) of 1-(butylcarbamoyl)-1,3-dihydrobenzimidazole-2-thione as white crystals: mp 179-180° C.

Workup

  1. customequipped with a condenser
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. filtrationthe solid was filtered
  4. washwashed with hexane
  5. customdried under vacuum

Sources & evidence

ORD record
ord-a60d163a99f840a2a0e590e2caae0f6c
Source dataset
uspto-grants-2000_07
Patent number
US06093738

Reaction notes

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