Potassium cyanate → 1-[1-(2-Chlorophenyl)-2-nitroethyl]urea

HRID 709138Notes

Reaction equation

HRID 709138 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([NH2:14])[CH2:10][N+:11]([O-:13])=[O:12].[O-:15][C:16]#[N:17].[K+]>O.CO>[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([NH:14][C:16]([NH2:17])=[O:15])[CH2:10][N+:11]([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 11378442Potassium cyanateHCID 866947771-(2-Chlorophenyl)-2-nitroethanamine hydrochloride

Product 1

HCID 680324091-[1-(2-Chlorophenyl)-2-nitroethyl]urea

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
40 °C

Procedure

At RT, 300 mg (about 93% pure, 1.18 mmol) of the compound of Example 25A were initially charged in 12 ml of water/methanol (1:1 v/v), and 287 mg (3.53 mmol) of potassium cyanate were added. The reaction mixture was warmed to 40° C. for 1 h. After cooling to RT, the mixture was directly separated into its components by preparative HPLC [Method 8]. This gave 120 mg (41% of theory) of the title compound.

Workup

  1. temperatureAfter cooling to RT
  2. customthe mixture was directly separated into its components by preparative HPLC [Method 8]

Sources & evidence

ORD record
ord-96a4bc65a8ce4fffb7c64e0a35592eb5
Source dataset
uspto-grants-2015_11
Patent number
US09180120B2

Reaction notes

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