Isoniazid → HCID 11625121, compound

HRID 732149Notes

Reaction equation

HRID 732149 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]=[C:11]([CH2:13][N:14]([CH3:20])[C:15](=[N:18][CH3:19])SC)[O:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:21]([NH:29][NH2:30])(=O)[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1>C(O)C.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]=[C:11]([CH2:13][N:14]([CH3:20])[C:15]3[N:18]([CH3:19])[C:21]([C:22]4[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=4)=[N:29][N:30]=3)[O:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 3767IsoniazidHCID 57837992HCID 57837992, compound

Product 1

HCID 11625121HCID 11625121, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

1-[3-(3-chloro-phenyl)-[1,2,4]oxadiazol-5-ylmethyl]-1,2,3-trimethyl-isothiourea (55 mg, 0.177 mmol) was mixed with isonicotinic hydrazide (29.1 mg, 0.212 mmol) in ethanol (1 mL) at 85° C. o.n. The reaction mixture was diluted with DCM and washed with water. The product was purified by column chromatography with 5˜7% MeOH in EA and triturated with Et2O to give the title compound (22.5 mg, 40%). 1H-NMR: 8.80 (d, 2H), 8.10 (s, 1H), 8.00 (d, 1H), 7.66 (d, 2H), 7.51 (d, 1H), 7.47(t, 1H), 4.80 (s, 2H), 3.74 (s, 3H), 3.15 (s, 3H).

Workup

  1. washwashed with water
  2. customThe product was purified by column chromatography with 5˜7% MeOH in EA
  3. customtriturated with Et2O

Sources & evidence

ORD record
ord-f7af0b21747a420aa3f49af4a441a04f
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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