Hydrochloric Acid → 1,4-Benzenediamine, N1,N1-bis(2-chloroethyl)-, hydrochloride (1:?)

HRID 2393776Notes

Reaction equation

HRID 2393776 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([N:8]([CH2:12][CH2:13][Cl:14])[CH2:9][CH2:10][Cl:11])=[CH:6][CH:5]=1)([O-])=O.Cl>C(OCC)(=O)C.CO.[Pd]>[ClH:11].[Cl:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][Cl:14])[C:7]1[CH:15]=[CH:16][C:4]([NH2:1])=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 23797755743-71-0

Product 1

HCID 2157271,4-Benzenediamine, N1,N1-bis(2-chloroethyl)-, hydrochloride (1:?)Yield 160%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Nitro-[N,N-bis(2-chloroethyl)]aniline (5.0 g; 19.0 mmol) was dissolved in a mixed solvent of 50 ml of ethyl acetate and 25 ml of methanol, followed by the addition of 5.0 ml of 4N hydrochloric acid. Using 10% Pd/C, the reactant was subjected to hydrogenation under normal pressure at room temperature. The Pd/C was filtered off and the solvent was distilled out. The residue was crystallized from ethanol-ethyl ether, whereby 4.1 g (15.2 mmol) of the title compound was obtained (yield: 80%). m.p. 230°-233° C.

Workup

  1. customwas subjected to hydrogenation under normal pressure at room temperature
  2. filtrationThe Pd/C was filtered off
  3. distillationthe solvent was distilled out
  4. customThe residue was crystallized from ethanol-ethyl ether

Sources & evidence

ORD record
ord-c4af0e47c10d45d6a1bb695fb3927b79
Source dataset
uspto-grants-1998_09
Patent number
US05808087

Reaction notes

Loading…