Aniline → HCID 9929751, compound

HRID 847402Notes

Reaction equation

HRID 847402 reaction equation
[CH3:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][Se:7][C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=O)=[CH:4][CH:3]=1.C(N(CC)CC)C.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.[NH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>ClCCl>[C:42]1([NH:41][C:10](=[O:12])[C:9]2[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=2[Se:7][CH2:6][C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:18][CH:17]=2)[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 8471Triethylamine2×HCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 19881348HCID 19881348, compound

Product 1

HCID 9929751HCID 9929751, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 1.58 g (0.00517 mol) 2-(4-methylbenzylseleno)benzoic acid (example 2) and 0.58 g (0.00573 mol) triethylamine in 10 ml dichloromethane which has been cooled to 0° C. is added 1.32 g (0.00517 mol) solid bis[2-oxo-3-oxazolidinyl]phosphoryl chloride in one portion. After stirring for 30 minutes a solution of 0.48 g aniline (0.47 ml; 0.00517 mol) in 10 ml dichloromethane and 0.74 g (1.02 ml; 0.00573 mol) triethylamine in 10 ml dichloromethane is added dropwise with stirring. The reaction mixture is stirred for 20 hours at room temperature and treated with 20 ml distilled water. The organic phase is separated and extracted successively with 20 ml water, two 25 ml portions of 10% hydrochloric acid and two 25 ml portions of 10% sodium hydroxide solution and dried. The solvent is then removed and the residue purified by column chromatography (silica gel/dichloromethane).

Workup

  1. additionis added dropwise
  2. stirringThe reaction mixture is stirred for 20 hours at room temperature
  3. additiontreated with 20 ml
  4. distillationdistilled water
  5. customThe organic phase is separated
  6. extractionextracted successively with 20 ml water, two 25 ml portions of 10% hydrochloric acid and two 25 ml portions of 10% sodium hydroxide solution
  7. customdried
  8. customThe solvent is then removed
  9. customthe residue purified by column chromatography (silica gel/dichloromethane)

Sources & evidence

ORD record
ord-ded652e16f4549c38846e67ebbc40176
Source dataset
uspto-grants-1992_08
Patent number
US05141955

Reaction notes

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