Hydrazine hydrate (1:1) → HCID 21069852, compound

HRID 1664137Notes

Reaction equation

HRID 1664137 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1([C:6]2[CH:7]=[C:8]([CH:21]=[CH:22][CH:23]=2)[CH2:9][N:10]2C(=O)C3C(=CC=CC=3)C2=O)[NH:5][NH:4]1.O.NN.FC(F)(F)C1(C2C=C(CN)C=CC=2)N=N1>C(O)C>[F:25][C:2]([F:1])([F:24])[C:3]1([C:6]2[CH:7]=[C:8]([CH2:9][NH2:10])[CH:21]=[CH:22][CH:23]=2)[NH:4][NH:5]1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 21069796HCID 21069796, compoundHCID 21069851HCID 21069851, compound

Product 1

HCID 21069852HCID 21069852, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 2-[3-(3-trifluoromethyl-diaziridin-3-yl)-benzyl]-isoindole-1,3-dione, (150 mg, 0.43 mmol) in ethanol (2 mL) was treated with hydrazine hydrate (0.4 mL) at room temperature and the solution stirred for 3.5 hrs. After removing ethanol in vacuo, the residue was partitioned between CH2Cl2 and water. The aqueous phase was acidified with dilute HCl, and washed with CH2Cl2. The aqueous phase was basified with dilute NaOH, and extracted with CH2Cl2. The organic extract was dried (MgSO4), filtered, and concentrated to obtain 50 mg (Yield 54%) of (3-(3-(trifluoromethyl)diaziridin-3-yl)phenyl)methanamine and (3-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)methanamine as a 1:1 mixture; 1H NMR (300 MHz, CDCl3) δ ppm: 3.85 (2H, s) 3.88 (2H, s) 7.08 (2H, s) 7.31-7.40 (4H, m) 7.43-7.50 (1H, m, J=6.2 Hz) 7.54 (1H, s); LC/MS m/z 216 (M+H for diazirine) and 218 (M+H for diaziridine).

Workup

  1. customAfter removing ethanol in vacuo
  2. customthe residue was partitioned between CH2Cl2 and water
  3. washwashed with CH2Cl2
  4. extractionextracted with CH2Cl2
  5. extractionThe organic extract
  6. dry with materialwas dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-09d0f031c37043ec9e0619b3ec3c4ecf
Source dataset
uspto-grants-2011_10
Patent number
US08039458B2

Reaction notes

Loading…