Stannous chloride dihydrate → HCID 53891383, compound

HRID 1729082Notes

Reaction equation

HRID 1729082 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([CH2:14][CH3:15])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[CH:6]=1.O.O.Cl[Sn]Cl>Cl>[Cl:1][CH2:2][CH2:3][N:4]([C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[NH2:11])[CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 22096740HCID 22096740, compound

Product 1

HCID 53891383HCID 53891383, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
90 °C

Procedure

A solution of the above nitro mustard (XII; R=H) (2.51 g, 11 mmol) in 12 N HCl (25 mL) was treated portionwise at 25 ° C. with SnCl2.2H2O (9.9 g, 44 mmol), heated on a steam bath at 90° C. for 1 h, then evaporated to dryness under reduced pressure. The residue as shaken vigorously With a mixture of CH2Cl2, 2 N NH4OH and ice, and filtered through a celite pad. Workup of the organic layer gave essentially pure 3-[N-(2-chloroethyl) -N-ethylamino]aniline (XIII; R=H) (1.92 g, 88%) as an oil, which was used immediately.

Workup

  1. customevaporated to dryness under reduced pressure
  2. filtrationfiltered through a celite pad

Sources & evidence

ORD record
ord-6fb4fcb80634494a8f5f7cfdf72241ed
Source dataset
uspto-grants-1994_07
Patent number
US05331004

Reaction notes

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