Aniline → HCID 9844425, compound

HRID 847404Notes

Reaction equation

HRID 847404 reaction equation
[CH2:1]([Se:8][C:9]1[C:17]2[O:18][CH2:19][O:20][C:16]=2[CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O)[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.[NH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>ClCCl>[CH2:1]([Se:8][C:9]1[C:17]2[O:18][CH2:19][O:20][C:16]=2[CH:15]=[CH:14][C:10]=1[C:11]([NH:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 8471Triethylamine2×HCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 19881352HCID 19881352, compound

Product 1

HCID 9844425HCID 9844425, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 1.6 g (0.0048 mol) 2-benzylseleno-3,4-methylenedioxybenzoic acid and 0.48 g triethylamine in 50 ml dichloromethane at 0° C. is added in one portion 1.22 g (0.0048 mol) solid bis[2-oxo-3-oxazolidinyl]phosphoryl chloride. After stirring for 30 min 0.44 g (0.44 ml) aniline in 5 ml dichloromethane are added at 0° C. dropwise with stirring followed after 1 hour by a solution of 0.48 g (0.66 ml) triethylamine in 10 ml dichloromethane. After 90 minutes at room temperature the reaction mixture is extracted successively with 50 ml 1N HCl and 50 ml water. The organic phase is dried over sodium sulfate and the solvent removed in vacuum. The crude product is purified by recrystallization from 2-propanol.

Workup

  1. additionare added at 0° C. dropwise
  2. extractionAfter 90 minutes at room temperature the reaction mixture is extracted successively with 50 ml 1N HCl and 50 ml water
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customthe solvent removed in vacuum
  5. customThe crude product is purified by recrystallization from 2-propanol

Sources & evidence

ORD record
ord-aa81febdcf26409582c805d6383294c1
Source dataset
uspto-grants-1992_08
Patent number
US05141955

Reaction notes

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