O-Xylene → HCID 178447200, compound

HRID 1953161Notes

Reaction equation

HRID 1953161 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:8]=[CH:7][C:5]=2[N:6]=1.C(N=C=[O:25])CCC.[CH3:26][C:27]1C=C[CH:30]=[CH:31][C:32]=1C>CCCCCC>[CH2:31]([C:30]([N:6]1[C:5]2[CH:7]=[CH:8][C:9]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:10][C:4]=2[N:3]=[C:2]1[SH:1])=[O:25])[CH2:32][CH2:27][CH3:26]

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 8110Butyl isocyanateHCID 178452643HCID 178452643, compound

Product 1

HCID 178447200HCID 178447200, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
147.5 °C

Procedure

To a slurry of 2-mercapto-5-(tert-butoxycarbonyl) aminobenzimidazole (11.46 g, 43.19 mmol) in o-xylene (50 mL) pre-heated to 100° C. was added n-butyl isocyanate (7.3 mL, 64.79 mmol) via syringe. The mixture was then heated at 145-150° C. for 1.5 h, then cooled to room temperature and diluted with hexane (200 mL). The solid was collected by suction filtration and dried under vacuum to afford 1-butylcarbonyl-2-mercapto-5-(tert-butoxycarbonyl)aminobenzimidazole (14.19 g, 95%). 1H-NMR (DMSO)δ: 0.94 (t, J=7.2 Hz, 3H), 1.20-1.60 (m, 4H, 2CH2), 1.51 (s, 9H), 3.37-3.43 (m, 2H, CH2N), 7.19-7.23 (dd, J=9.0 and 1.9 Hz, 1H, Ar-H), 7.64 (s, 1H), 7.96 (d, J=9.0 Hz, 1H, Ar-H), 9.59 (s, 1H), 10.22 (t, J=5.4 Hz, 1H, NHCH2). Elemental Analysis calc (found %: C, 56.0 (55.8); H, 6.6 (5.7) and N, 15.4 (15.3).

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe solid was collected by suction filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-10678ebaa31d49ee98b186f0902d6680
Source dataset
uspto-grants-2000_09
Patent number
US06114537

Reaction notes

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