Triphenylphosphine → 2-(2-Amino-ethoxy)-4-chloro-6-nitro-phenylamine

HRID 1872847Notes

Reaction equation

HRID 1872847 reaction equation
[N:1]([CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[C:9]([N+:14]([O-:16])=[O:15])[C:8]=1[NH2:17])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O>[NH2:1][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[C:9]([N+:14]([O-:16])=[O:15])[C:8]=1[NH2:17]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 186876782-(2-Azido-ethoxy)-4-chloro-6-nitro-phenylamine

Product 1

HCID 186876792-(2-Amino-ethoxy)-4-chloro-6-nitro-phenylamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(2-azido-ethoxy)-4-chloro-6-nitro-phenylamine (1.9 g, 7.36 mmol) and triphenylphosphine (2.27 g, 8.65 mmol) in tetrahydrofuran (80 ml) and water (2 ml) was allowed to stir for 24 hours at room temperature. The solvent was removed under vacuum and the solid washed with methylene chloride (30 ml) to afford an orange solid: mp 156-157° C.

Workup

  1. customThe solvent was removed under vacuum
  2. washthe solid washed with methylene chloride (30 ml)
  3. customto afford an orange solid

Sources & evidence

ORD record
ord-70b65f6fa602491f94be4d4935905255
Source dataset
uspto-grants-2000_08
Patent number
US06110956

Reaction notes

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