Sulfuric Acid → HCID 136492349, compound

HRID 59256Notes

Reaction equation

HRID 59256 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[NH:13][C:12](=[O:14])[N:11]([C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=2)[N:10]=1.S(=O)(=O)(O)[OH:24]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[NH:13][C:12](=[O:14])[N:11]([C:15]2[CH:22]=[CH:21][C:18]([C:19]([NH2:20])=[O:24])=[CH:17][CH:16]=2)[N:10]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 136644910HCID 136644910, compound

Product 1

HCID 136492349HCID 136492349, compound

Procedure

A solution of 4-(3-(2-chloro-6-fluorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)benzonitrile (1.0 g, 0.003 mol) in conc. sulphuric acid (10 mL) was heated to 70° C. for 15 h. The reaction mixture was quenched in ice water. The reaction mass was basified till pH˜6-6.5 with dilute NaOH. The obtained solid was filtered off, washed with water and suck dried to afford 0.300 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 7.36 (br s, 1H), 7.84 (t, 1H), 7.57 (d, 1H), 7.67 (d, 1H), 7.98 (m, 5H), 12.70 (br s, 1H); MS (m/z): 333.11 (M+H)+.

Workup

  1. customThe reaction mixture was quenched in ice water
  2. filtrationThe obtained solid was filtered off
  3. washwashed with water and suck
  4. customdried

Sources & evidence

ORD record
ord-5f4306599b034335b9c165a07fb1b1c6
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

Loading…