2-Nitro-4-(trifluoromethyl)benzamide → 4'-(2,2,2-trifluoroethoxy)-7-(trifluoromethyl)-1H-spiro[quinazolin-2,1'-cyclohexan]-4(3H)-one

HRID 1469217Notes

Reaction equation

HRID 1469217 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:5]=1[C:6]([NH2:8])=[O:7])([O-])=O.[F:17][C:18]([F:29])([F:28])[CH2:19][O:20][CH:21]1[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]1.O.[Sn](Cl)Cl>C1(C)C=CC=CC=1>[F:17][C:18]([F:28])([F:29])[CH2:19][O:20][CH:21]1[CH2:26][CH2:25][C:24]2([NH:8][C:6](=[O:7])[C:5]3[C:4](=[CH:12][C:11]([C:13]([F:16])([F:15])[F:14])=[CH:10][CH:9]=3)[NH:1]2)[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 27757792-Nitro-4-(trifluoromethyl)benzamideHCID 43835034Tin dichloride dihydrateHCID 595627824-(2,2,2-Trifluoroethoxy)cyclohexanone

Product 1

HCID 866666784'-(2,2,2-trifluoroethoxy)-7-(trifluoromethyl)-1H-spiro[quinazolin-2,1'-cyclohexan]-4(3H)-oneYield 39.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Nitro-4-trifluoromethylbenzamide (347 mg, 1.47 mmol), 4-(2,2,2-trifluoroethoxy)cyclohexanone (303 mg, 1.54 mmol) and tin(II) chloride hydrate (663 mg, 2.94 mmol) were added to toluene (5 ml) under argon and stirred under reflux conditions for 10 h. After cooling to room temperature, filtration with suction and thorough drying of the solid which precipitated gave 4′-(2,2,2-trifluoroethoxy)-7-(trifluoromethyl)-1H-spiro[quinazolin-2,1′-cyclohexan]-4(3H)-one (223 mg, 36% of theory) as a colorless solid. 1H NMR (400 MHz, d6-DMSO δ, ppm) 8.23 (br. 5, 1H, NH), 7.73 (d, 1H), 7.21 (br. s, 1H, NH), 7.19 (s, 1H), 6.90 (d, 1H), 4.06 (q, 2H), 3.51 (m, 1H), 1.90 (m, 4H), 1.62 (m, 4H).

Workup

  1. filtrationfiltration with suction
  2. customthorough drying of the solid which
  3. customprecipitated

Sources & evidence

ORD record
ord-5fa579518de14fe5a9a2786afe855bc6
Source dataset
uspto-grants-2015_04
Patent number
US09006265B2

Reaction notes

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