Diisopropylethylamine → HCID 18468203, compound

HRID 457992Notes

Reaction equation

HRID 457992 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6](Cl)=[O:7].C([N:15](CC)[CH:16]([CH3:18])C)(C)C.Cl.C(#[N:24])C>ClCCl>[C:16]([CH2:18][NH:24][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[CH:3][C:4]=1[OH:11])#[N:15]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 184681274-Fluoro-2-hydroxybenzoyl chlorideHCID 22261314Acetonitrile--hydrogen chloride (1/1)

Product 1

HCID 18468203HCID 18468203, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
35 °C

Procedure

A solution of 4-fluorosalicylic acid chloride (Example 1, 10 g, 57.3 mmol) in dichloromethane (114 mL) was treated with N,N-diisopropylethyl amine (25 mL, 143 mmol) and acetonitrile hydrochloride (7.95 g, 85.9 mmol). After stirring at 35° C. for 24 h, the solution was concentrated under reduced pressure, diluted with ethyl acetate, and washed successively with 2 N HCl and saturated aq NaCl. The resulting solution was dried over MgSO4, filtered and concentrated. The resulting solid was suspended in dichloromethane, filtered and rinsed with heptane to give N-cyanomethyl-4-fluoro-2-hydroxy-benzamide (7.20 g, 65%): 1H NMR (DMSO-d6 300 MHz) δ 12.16 (br s, 1 H), 9.17 (t, J=5.3 Hz, 1 H), 7.88 (dd, J, =8.7 Hz, J2=6.3 Hz, 1 H), 6.81–6.73 (m, 2 H), 4.32 (d, J=5.7 Hz, 2 H).

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. additiondiluted with ethyl acetate
  3. washwashed successively with 2 N HCl and saturated aq NaCl
  4. dry with materialThe resulting solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. filtrationfiltered
  8. washrinsed with heptane

Sources & evidence

ORD record
ord-d541495d1e6d498c84c702e372ada1e4
Source dataset
uspto-grants-2007_03
Patent number
US07189749B2

Reaction notes

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