Cyanuric chloride → HCID 59659978, compound

HRID 2057069Notes

Reaction equation

HRID 2057069 reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5]([Cl:6])=[N:4][C:2]=1Cl.[CH2:10]([O:17][C:18]1[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][C:19]=1[Cl:25])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[Na+]>CC(C)=O>[CH2:10]([O:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:2]2[N:1]=[C:8]([Cl:9])[N:7]=[C:5]([Cl:6])[N:4]=2)=[CH:20][C:19]=1[Cl:25])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 14798Sodium Hydroxide2×HCID 12682854-Benzyloxy-3-chloroaniline

Product 1

HCID 59659978HCID 59659978, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
2.5 °C

Procedure

To cyanuric chloride (1.208 g, 6.4 mmol) dissolved in acetone (10 mL) stirring at 0-5° C., was added a solution of 160a (1.505 g, 6.4 mmol) in acetone (15 mL) followed by the addition of 2.5 N NaOH (2.6 mL, 6.4 mmol). The reaction mixture was allowed to stir at 0-5° C. for 1 h under nitrogen. The reaction mixture was poured over crushed ice and neutralized with 5% NaOH. The solid that formed was collected by vacuum filtration and the resulting solid was dried overnight under vacuum. Flash column chromatography (SiO2, 70:30 hexanes:ethyl acetate) yielded a light beige solid (160b, 1.46 g, 60%), mp 145° C.; HPLC: Inertsil ODS-3V C18, 40:30:30 [KH2PO4 (0.01M, pH 3.2): CH3OH: CH3CN], 264 nm, Rt 111.2 min, 97.1% purity.

Workup

  1. stirringto stir at 0-5° C. for 1 h under nitrogen
  2. additionThe reaction mixture was poured
  3. customover crushed ice
  4. customThe solid that formed
  5. filtrationwas collected by vacuum filtration
  6. customthe resulting solid was dried overnight under vacuum

Sources & evidence

ORD record
ord-bf4cfcaeb282452397834b918e27320e
Source dataset
uspto-grants-2008_02
Patent number
US07335770B2

Reaction notes

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