Water → HCID 59656698, compound

HRID 2054906Notes

Reaction equation

HRID 2054906 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][C:11]1[CH:19]=[C:18]([F:20])[C:14]([C:15]([NH2:17])=O)=[C:13]([F:21])[CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].N1C(Cl)=NC(Cl)=NC=1Cl.O>CN(C=O)C>[C:1]([NH:8][CH2:9][CH2:10][C:11]1[CH:12]=[C:13]([F:21])[C:14]([C:15]#[N:17])=[C:18]([F:20])[CH:19]=1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 7954Cyanuric chlorideHCID 59656711HCID 59656711, compound

Product 1

HCID 59656698HCID 59656698, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of the above benzamide intermediate (1.5 g, 5.0 mmol) in DMF (15 mL) at 0° C. was added cyanuric chloride (0.461 g, 2.5 mmol). The reaction was stirred at 0° C. for 40 min. Water (50 mL) was added and the mixture was extracted with dichloromethane, dried with sodium sulfate and concentrated. Chromatography on silica gel (ether/hexane, 1:1) afforded 4-(N-boc-2-aminoethyl)-2,6-difluorobenzonitrile (1.1 g, 3.9 mmol, 78%).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialdried with sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c21ef66dd07b45dfb267e0219b565562
Source dataset
uspto-grants-2008_02
Patent number
US07329764B2

Reaction notes

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