4-Fluorobenzaldehyde → HCID 178509510, compound

HRID 1919744Notes

Reaction equation

HRID 1919744 reaction equation
S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].[F:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1.[NH2:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[NH2:28])[C:23]#[N:24]>O.C(O)C.CN(C=O)C>[F:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]2[NH:28][C:27]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][C:20]=3[N:19]=2)=[CH:13][CH:12]=1

Participants

7

Reactant 3

HCID 680234-FluorobenzaldehydeHCID 656671Sodium PyrosulfiteHCID 7372853,4-Diaminobenzonitrile

Product 1

HCID 178509510HCID 178509510, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

Sodium metabisulfite (1.66 g, 8.73 mmol) in 10 ml of water was added to 4-fluoro-benzaldehyde (1.86 g, 15 mmol) in 50 ml of ethanol under argon. The mixture was stored at 0-5° C. overnight and the solid filtered, washed with ethanol and dried. The solid and 3,4-diamino-benzonitrile (2.0 g, 15 mmol) were heated in 7 ml of DMF at 130° C. for 4 hours. After cooling, the mixture was poured into water, the solid filtered and purified by preparative HPLC (RP18, acetonitrile/water 0.1% TFA) to yield 2.49 g (70%) of the desired product. MS (mass spectrum): m/e=238.02 (M+H+).

Workup

  1. filtrationthe solid filtered
  2. washwashed with ethanol
  3. customdried
  4. temperatureAfter cooling
  5. filtrationthe solid filtered
  6. custompurified by preparative HPLC (RP18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-07781f5b8a794b6295f8703a9ee7f8d0
Source dataset
uspto-grants-2012_05
Patent number
US08168665B2

Reaction notes

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