Benzoyl isothiocyanate → HCID 11558516, compound

HRID 536111Notes

Reaction equation

HRID 536111 reaction equation
C([N:9]=[C:10]=[S:11])(=O)C1C=CC=CC=1.C(O[C:15]([C:17]1[NH:18][CH:19]=[C:20]([Br:27])[C:21]=1[NH:22][CH2:23][CH:24]([CH3:26])[CH3:25])=[O:16])C>C(Cl)Cl>[Br:27][C:20]1[C:21]2[N:22]([CH2:23][CH:24]([CH3:25])[CH3:26])[C:10](=[S:11])[NH:9][C:15](=[O:16])[C:17]=2[NH:18][CH:19]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 67068492HCID 67068492, compound

Product 1

HCID 11558516HCID 11558516, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzoyl isothiocyanate (0.034 g, 0.2 mmol) was added to a solution of 4-bromo-3-(isobutylamino)-1H-pyrrole-2-carboxylic acid ethyl ester (0.050 g, 0.17 mmol) in CH2Cl2 and the resulting mixture was stirred at r.t. for 1 h before it was concentrated in vacuo. The residue was dissolved in ammonia (7M in methanol, 1.5 mL) and stirred at 70° C. for 4 h. Additional ammonia (7M in methanol, 1 mL) was added and the mixture was stirred at 80° C. for 5 h. The mixture was cooled to r.t. and the precipitated product was filtered and washed with diethyl ether. After recrystallization with methanol the title compound (0.028 g, 55%) was obtained as a white solid.

Workup

  1. concentrationwas concentrated in vacuo
  2. dissolutionThe residue was dissolved in ammonia (7M in methanol, 1.5 mL)
  3. stirringstirred at 70° C. for 4 h
  4. additionAdditional ammonia (7M in methanol, 1 mL) was added
  5. stirringthe mixture was stirred at 80° C. for 5 h
  6. temperatureThe mixture was cooled to r.t.
  7. filtrationthe precipitated product was filtered
  8. washwashed with diethyl ether
  9. customAfter recrystallization with methanol the title compound (0.028 g, 55%)
  10. customwas obtained as a white solid

Sources & evidence

ORD record
ord-9700d21ec7154a4eb70f51bc7bad9bc1
Source dataset
uspto-grants-2014_10
Patent number
US08859568B2

Reaction notes

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