Acetic Acid → Azafenidin

HRID 725202Notes

Reaction equation

HRID 725202 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH2:10][C:11]#[CH:12])=[CH:4][C:3]=1[NH:13][N:14]=[C:15]1[CH2:20][CH2:19][CH2:18][CH2:17][N:16]1[C:21]([O:23]C)=O.C(O)(=O)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH2:10][C:11]#[CH:12])=[CH:4][C:3]=1[N:13]1[C:21](=[O:23])[N:16]2[CH2:17][CH2:18][CH2:19][CH2:20][C:15]2=[N:14]1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 86751850HCID 86751850, compound

Product 1

HCID 443029AzafenidinYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 10.0 g of the product from Step B and 0.50 g of glacial acetic acid in 50 mL of toluene is heated at 100° C. for 2 h while removing methanol vapor with a stream of nitrogen. Hexane (50 mL) is added at 70° C. and the product is filtered at 25° C. and washed with hexanes to provide 8.0 g (94%) of the title compound, m.p. 168°-169° C. 1H NMR (CDCl3) δ1.9 (m, 4H), 2.55 (t, 1H, J=2.4Hz), 2.74 (t, 2H, J=6Hz), 3.67 (t, 2H, J=6Hz), 4.74 (d, 2H, J=2.4Hz), 7.13 (s, 1H), 7.50 (s, 1H).

Workup

  1. customwhile removing methanol vapor with a stream of nitrogen
  2. additionHexane (50 mL) is added at 70° C.
  3. filtrationthe product is filtered at 25° C.
  4. washwashed with hexanes

Sources & evidence

ORD record
ord-d857b239e85f4a4a92b1107964e3160e
Source dataset
uspto-grants-1998_01
Patent number
US05705639

Reaction notes

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