Benzoyl isothiocyanate → N-(1H-benzimidazol-2-ylmethyl)thiourea

HRID 912664Notes

Reaction equation

HRID 912664 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]1[NH:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1.CCN(C(C)C)C(C)C.C1C=CC(C([N:31]=[C:32]=[S:33])=O)=CC=1>ClCCl>[NH:9]1[C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[N:6]=[C:5]1[CH2:4][NH:3][C:32]([NH2:31])=[S:33]

Participants

5

Reactant 3

HCID 68284Benzoyl isothiocyanateHCID 81531DiisopropylethylamineHCID 2723957(1H-benzo[d]imidazol-2-yl)methanamine dihydrochloride

Product 1

HCID 86631117N-(1H-benzimidazol-2-ylmethyl)thioureaYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-(Aminomethyl)benzimidazole dihydrochloride (0.66 g, 3.0 mmol) in dichloromethane (10 mL) was added DIPEA (1.05 mL, 6.0 mmol). The reaction mixture was stirred for 5 minutes and then benzoyl isothiocyante (0.44 mL, 3.3 mmol) was added dropwise. The resulting mixture was stirred for 1 h and then evaporated in vacuo. Ammonia (saturated, in MeOH, 15 mL) was added to the residue. After 4 h the reaction mixture was evaporated. Addition of CH2Cl2 to the residue afforded a solid, which was collected by filtration, washed with dichloromethane and dried to give the title compound (0.38 g, 62%). 1H NMR (DMSO-d6) δ ppm 12.32 (1H), 8.17 (1H), 7.52-7.19 (4H), 4.83 (2H); MS (ESI) m/z 205 (M−1).

Workup

  1. stirringThe resulting mixture was stirred for 1 h
  2. customevaporated in vacuo
  3. additionAmmonia (saturated, in MeOH, 15 mL) was added to the residue
  4. customAfter 4 h the reaction mixture was evaporated
  5. additionAddition of CH2Cl2 to the residue
  6. customafforded a solid, which
  7. filtrationwas collected by filtration
  8. washwashed with dichloromethane
  9. customdried

Sources & evidence

ORD record
ord-000ef65fcaf94f06acf59c2f6875413d
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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