Benzoyl isothiocyanate → 4-{[(benzoylamino)carbonothioyl][(2-butyl-4-chloro-1H-imidazol-5-yl)methlyl]amino}-1H-imidazole-5-carboxamide

HRID 912662Notes

Reaction equation

HRID 912662 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]([CH2:11][NH:12][C:13]2[N:14]=[CH:15][NH:16][C:17]=2[C:18]([NH2:20])=[O:19])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].[C:21]([N:29]=[C:30]=[S:31])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)Cl.CO>[C:21]([NH:29][C:30]([CH:11]([NH:12][C:13]1[N:14]=[CH:15][NH:16][C:17]=1[C:18]([NH2:20])=[O:19])[C:7]1[NH:6][C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:9][C:8]=1[Cl:10])=[S:31])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 674141614-{[(2-Butyl-4-chloro-1H-imidazol-5-yl)methyl]amino}-1H-imidazole-5-carboxamide

Product 1

HCID 1317291954-{[(benzoylamino)carbonothioyl][(2-butyl-4-chloro-1H-imidazol-5-yl)methlyl]amino}-1H-imidazole-5-carboxamideYield 38%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

4-{[(2-Butyl-4-chloro-1H-imidazol-5-yl)methyl]amino}-1H-imidazole-5-carboxamide (0.30 g, 1.01 mmol, obtained from Example 7(a)) was dissolved in CH2Cl2 (5 mL) and methanol (2 mL). Benzoylisothiocyanate (0.18 g, 1.11 mmol) was added and the mixture was stirred at r.t. for 4 h. The mixture was then concentrated in vacuo and dissolved in ethyl acetate and washed with water. The aqueous phase was extracted twice with ethyl acetate and the combined organic layers were dried (MgSO4) and concentrated. The crude product was purified by flash column chromatography (CH2Cl2/methanol gradient; 0 to 20% methanol), obtaining 0.175 g (38%) of the title compound. MS (ESI) m/z 460 (M+1).

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. dissolutiondissolved in ethyl acetate
  3. washwashed with water
  4. extractionThe aqueous phase was extracted twice with ethyl acetate
  5. dry with materialthe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by flash column chromatography (CH2Cl2/methanol gradient; 0 to 20% methanol)

Sources & evidence

ORD record
ord-1a9c1ad27aa14b9cb4ccd4b515516c50
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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