Methylurea → HCID 59828850, compound

HRID 1190950Notes

Reaction equation

HRID 1190950 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7](=O)[CH2:8]Br)=[CH:5][CH:4]=1)#[N:2].[CH3:13][NH:14][C:15]([NH2:17])=[O:16]>CN(C=O)C.CCCCCC.CCOC(C)=O>[CH3:13][NH:14][C:15]1[O:16][CH:8]=[C:7]([C:6]2[CH:11]=[CH:12][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[N:17]=1

Participants

5

Reactant 2

HCID 11719MethylureaHCID 986544-(Bromoacetyl)benzonitrile

Product 1

HCID 59828850HCID 59828850, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Dissolve 4-cyanophenacyl bromide (10 g, 44.6 mmol) and methylurea (6.5 g, 89.3 mmol) in DMF (125 mL). Stir the reaction at 90° C. for 16 h under a nitrogen atmosphere. Cool to room temperature, dilute with hexane/EtOAc (1:1, 250 mL) and wash with 10% aqueous NaCl (4×75 mL). Collect the organic phase, concentrate in vacuo and purify the crude mixture by chromatography on silica gel (330 g) eluting with DCM/methanol (1:0 to 24:1 gradient) to obtain the desired intermediate (2.3 g, 26%). MS (ES+) m/z: 200.2 (M+H)+.

Workup

  1. customthe reaction at 90° C. for 16 h under a nitrogen atmosphere
  2. washwash with 10% aqueous NaCl (4×75 mL)
  3. customCollect the organic phase
  4. concentrationconcentrate in vacuo
  5. custompurify the crude mixture by chromatography on silica gel (330 g)
  6. washeluting with DCM/methanol (1:0 to 24:1 gradient)

Sources & evidence

ORD record
ord-22371bd8018f46b1b7fb88793086b0e5
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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