Cesium carbonate → Tert-butyl 2-(6-chloro-5-iodo-1H-benzo[d]imidazol-2-ylthio)acetate

HRID 2193844Notes

Reaction equation

HRID 2193844 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[Cl:16][C:17]1[C:26]([I:27])=[CH:25][C:20]2[NH:21][C:22](=[S:24])[NH:23][C:19]=2[CH:18]=1>C1COCC1>[Cl:16][C:17]1[C:26]([I:27])=[CH:25][C:20]2[N:21]=[C:22]([S:24][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[NH:23][C:19]=2[CH:18]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 574814685-Chloro-6-iodo-1H-benzo[d]imidazole-2(3H)-thione2×

Product 1

HCID 58387110Tert-butyl 2-(6-chloro-5-iodo-1H-benzo[d]imidazol-2-ylthio)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cs2CO3 (2.3 g, 7.08 mmol), followed by tert-butyl bromoacetate (0.52 mL, 3.54 mmol), was added to a solution of 5-chloro-6-iodo-1,3-dihydro-2H-benzimidazole-2-thione (Intermediate 7, 1.1 g, 3.54 mmol) in THF (20 mL) at 0° C. The reaction was stirred at rt for 0.5 h. Volatiles were removed and the residue was partitioned between EtOAc and water. Concentration afforded the desired product as a white power. LC-MS: calculated for C13H14ClIN2O2S 423.95, observed m/e 424.8 (M+H)+.

Workup

  1. customVolatiles were removed
  2. customthe residue was partitioned between EtOAc and water
  3. concentrationConcentration

Sources & evidence

ORD record
ord-6b87a6c4e77e41319861efed8e0bed76
Source dataset
uspto-grants-2012_12
Patent number
US08329914B2

Reaction notes

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