Cyanoacetic acid → 1-(2-Cyanoacetyl)-3-(2-fluoro-4-iodophenyl)-urea

HRID 75672

Reaction equation

HRID 75672 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([NH2:12])=[O:11].[C:13]([CH2:15][C:16](O)=[O:17])#[N:14].CS(Cl)(=O)=O.O.C(O)(C)C>CN(C)C=O>[C:13]([CH2:15][C:16]([NH:12][C:10]([NH:9][C:3]1[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=1[F:1])=[O:11])=[O:17])#[N:14]

Participants

6

Reactant 4

HCID 9740Cyanoacetic acidHCID 31297Methanesulfonyl chlorideHCID 21889133Propan-2-ol--water (1/1)HCID 59717008(2-Fluoro-4-iodophenyl)-urea

Product 1

HCID 597173171-(2-Cyanoacetyl)-3-(2-fluoro-4-iodophenyl)-urea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of (2-fluoro-4-iodophenyl)-urea 78 (21.7 g) and cyanoacetic acid 73 (7.88 g) in N,N-dimethylformamide (108 ml) was added, and methanesulfonyl chloride (7.17 ml) was added dropwise with stirring at room temperature. The mixture was stirred at room temperature for 2 hrs, and water-isopropyl alcohol [1:2 (volume ratio), 210 ml] was added dropwise. The mixture was stirred at room temperature for 1 hr. The precipitated crystals were collected by filtration and washed with water to give 1-(2-cyanoacetyl)-3-(2-fluoro-4-iodophenyl)-urea 79 (wet crystals), which was used for the next reaction in the form of wet crystals.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at room temperature for 2 hrs
  3. stirringThe mixture was stirred at room temperature for 1 hr
  4. filtrationThe precipitated crystals were collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-1a932bf29f6e486bba32a6e38f9030a0
Source dataset
uspto-grants-2014_09
Patent number
US08835443B2

Linked notes

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