4-Chloroaniline → HCID 178478211, compound

HRID 847401Notes

Reaction equation

HRID 847401 reaction equation
[CH2:1]([C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10](O)=[Se:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.[Cl:39][C:40]1[CH:46]=[CH:45][C:43]([NH2:44])=[CH:42][CH:41]=1>ClCCl>[Cl:39][C:40]1[CH:46]=[CH:45][C:43]([NH:44][C:10](=[Se:11])[C:9]2[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=2[CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:42][CH:41]=1

Participants

6

Reactant 4

HCID 78124-ChloroanilineHCID 8471Triethylamine2×HCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 178526205HCID 178526205, compound

Product 1

HCID 178478211HCID 178478211, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6 g (0.0206 mol) 2-benzylselenobenzoic acid and 2.1 g (0.0206 mol) triethylamine in 100 ml dichloromethane at 0°-5° C. is added in one portion 5.24 g (0.0206 mol) bis[2-oxo-3-oxazolidinyl]phosphoryl chloride. After stirring for 30 minutes a solution of 2.63 g (0.0206 mol) 4-chloroaniline at 0° C. is added and after 15 minutes a solution of 2.1 g (0.0206 mol) triethylamine in 30 ml dichloromethane (within 21/2 hours). The reaction mixture is then immediately extracted with 100 ml 1N aqueous hydrochloroic acid solution, 100 ml 1N caustic soda solution and 100 ml distilled water. The organic phase is dried with sodium sulfate and the solvent removed under vacuum. The residue is purified by recrystallization from 80 ml 2-propanol.

Workup

  1. extractionThe reaction mixture is then immediately extracted with 100 ml 1N aqueous hydrochloroic acid solution, 100 ml 1N caustic soda solution and 100 ml
  2. distillationdistilled water
  3. dry with materialThe organic phase is dried with sodium sulfate
  4. customthe solvent removed under vacuum
  5. customThe residue is purified by recrystallization from 80 ml 2-propanol

Sources & evidence

ORD record
ord-6b13b0d2097d4abea30e86b9283f84c9
Source dataset
uspto-grants-1992_08
Patent number
US05141955

Reaction notes

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