Methanol → HCID 70144866, compound

HRID 1281691Notes

Reaction equation

HRID 1281691 reaction equation
C([O:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][C@@H:7]([N:11]2[C:15]3[CH:16]=[C:17]([Cl:21])[C:18]([Cl:20])=[CH:19][C:14]=3[N:13]=[C:12]2[Br:22])[C@@H:6]1[O:23]C(=O)C)(=O)C.CO.O.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[Br:22][C:12]1[N:11]([C@@H:7]2[CH2:8][CH2:9][CH2:10][C@@H:5]([OH:4])[C@H:6]2[OH:23])[C:15]2[CH:16]=[C:17]([Cl:21])[C:18]([Cl:20])=[CH:19][C:14]=2[N:13]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 10340Sodium CarbonateHCID 86585504HCID 86585504, compound

Product 1

HCID 70144866HCID 70144866, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(±)-(1R*,2S*,3R*)-3-(2-Bromo-5,6-dichloro-1H-benzimidazol-1-yl)-1,2-cyclohexanediyl diacetate (part c of this example, 700 mg, 1.51 mmol) was dissolved in ethanol (12 ml)-methanol (12 ml)-water (3 ml). Sodium carbonate (160 mg, 1.5 mmol) was added and the mixture was stirred vigorously for 3 h. Volatiles were evaporated in vacuo and the residual solids were slurried in water. The solid was recrystallized from ethanol to give title compound as white powder (260 mg, 45%), m.p. 197-199° C. dec.; 1H-NMR (DMSO-d6, 200 MHz) δ: 8.26 and 7.92 (both s, each 1, 2 aromatic CH), 4.8-4.6 (m, 3, OCH and 2OH), 4.264.20 (m, 1, NCH), 4.17-3.98 (m, 1, OCH), 2.24-2.19 (m, 1, 1/2 CH2), 1.84-1.74 (m, 4, 2 CH2), 1.60-1.53 (m, 4, 1, 1/2 CH2).

Workup

  1. customVolatiles were evaporated in vacuo
  2. customThe solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-d2907926dfa3461eb2f3c2cd01cb6c8a
Source dataset
uspto-grants-2002_09
Patent number
US06455507B1

Reaction notes

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