Water → HCID 57481537, compound

HRID 422582Notes

Reaction equation

HRID 422582 reaction equation
[CH3:1][C:2]1[S:6][C:5]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][CH:3]=1.[Br:15]Br.O.[OH-].[Na+]>CO>[Br:15][C:4]1[CH:3]=[C:2]([CH3:1])[S:6][C:5]=1[NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24408BromineHCID 716045tert-butyl N-(5-methylthiophen-2-yl)carbamate

Product 1

HCID 57481537HCID 57481537, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl 5-methylthiophen-2-ylcarbamate (5.1 g, 23.91 mmol) in MeOH (478 mL) at 0° C. was added drop wise a solution of bromine (1.232 mL, 23.91 mmol) in MeOH (478 mL) during 1.5 h. The reaction mixture was then stirred at 0° C. for 0.5 h and at ambient temperature for 45 min. The reaction was poured into water (400 mL) and the solution was neutralized with 2 M NaOH (aq). MeOH was removed under reduced pressure and the cloudy aqueous phase was extracted with DCM (3×200 mL). The combined organic phases were dried over MgSO4. The solvent was removed under reduced pressure to give (5.3 g, 76%) of the title compound that was used in the next step without further purification: LC/MS (Table 1, Method a) Rt=2.48 min; m/z: 292.1 (M−H)−.

Workup

  1. customMeOH was removed under reduced pressure
  2. extractionthe cloudy aqueous phase was extracted with DCM (3×200 mL)
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-874a21d4ac6a40189f80fcd07b83995d
Source dataset
uspto-grants-2012_01
Patent number
US08101645B2

Reaction notes

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