Thionyl Chloride → 4-(Chloromethyl)-N-methyl-2-nitroaniline

HRID 256527Notes

Reaction equation

HRID 256527 reaction equation
[CH3:1][NH:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]O)=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12].S(Cl)([Cl:16])=O>>[CH3:1][NH:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][Cl:16])=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 12323420[4-(Methylamino)-3-nitrophenyl]methanol

Product 1

HCID 109765114-(Chloromethyl)-N-methyl-2-nitroanilineYield 55%

Procedure

1.0 g (5.5 mmol) of 9 was dissolved in 25 ml thionylchloride at -78° C. cooled with dry ice/acetone bath. After it dissolved completely, the dry ice/acetone bath was removed and the reaction mixture allowed to warm up to room temperature and kept at room temperature for additional 1 hour. Thionylchloride was evaporated under vacuum at room temperature and the residue was washed with 5 ml cold diethylether and recrystallized from diethylether to yield 0.6 g (55%) of 10. Yellow, mp: 126°-128° C. 1H NMR: (DMSO-d6): δ 82.9 (s, 1H, NH), 8.15 (d, 1H, J=2.2 Hz, H-2), 7.60p, 1H, (dd, 1H, J=8.9, 2.2 Hz, H-6), 7.01 (d, 1H, J=9.0 Hz, H-5), 4.76 (s, 3H, CH2), 2.95 (s, 3H, CH3). Anal. Calcd for C8H9N2O2Cl: C, 47.89; H, 4.52; Cl, 17.67; N, 14.00; O, 15.95. found: C, 47.78; H, 4.49; Cl, 17.78; N, 13.82; O, 16.13.

Workup

  1. temperaturecooled with dry ice/acetone bath
  2. dissolutionAfter it dissolved completely
  3. customthe dry ice/acetone bath was removed
  4. customThionylchloride was evaporated under vacuum at room temperature
  5. washthe residue was washed with 5 ml cold diethylether
  6. customrecrystallized from diethylether

Sources & evidence

ORD record
ord-819b806217ff444191a6f31ac531eb15
Source dataset
uspto-grants-1993_11
Patent number
US05258370

Reaction notes

Loading…