Acetic Acid → HCID 59402311, compound

HRID 2090341Notes

Reaction equation

HRID 2090341 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH:11][C:12](=[O:15])[O:13][CH3:14])[CH3:10])=[CH:4][CH:3]=1.C=O.S(=O)(=O)(O)O.[C:23](O)(=O)C>>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([CH2:8][CH:9]([CH3:10])[N:11]([C:12]([O:13][CH3:14])=[O:15])[CH2:23]2)=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 59402313Methyl [2-(4-bromophenyl)-1-methylethyl]carbamate

Product 1

HCID 59402311HCID 59402311, compoundYield 100.8%

Procedure

To a mixture of methyl [2-(4-bromophenyl)-1-methylethyl]carbamate (465 mg, 1.71 mmol) and paraformaldehyde (82.1 mg, 2.73 mmol) was added a mixture of concentrated sulfuric acid (2.5 mL, 47 mmol) and glacial acetic acid (3.75 mL, 66.0 mmol). The resulting mixture was stirred at r.t. overnight. The reaction mixture was poured into ice-water, and extracted with CH2Cl2. The organic layer was washed with water, saturated NaCO3 aqueous solution and brine, dried with MgSO4. After filtration, the filtrate was concentrated to afford the desired compound (490 mg, 100%) which was directly used in the next step reaction without further purification. LCMS (M+H)+: m/z=284.2.

Workup

  1. additionwas added
  2. extractionextracted with CH2Cl2
  3. washThe organic layer was washed with water, saturated NaCO3 aqueous solution and brine
  4. dry with materialdried with MgSO4
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-43e07e5a7212440e853a12d16a3de3f5
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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