Aniline → HCID 19890958, compound

HRID 893637Notes

Reaction equation

HRID 893637 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][Se:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O.C(N(CC)CC)C.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.[NH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>ClCCl>[C:41]1([NH:40][C:11](=[O:13])[C:10]2[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=2[Se:8][CH2:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 8471Triethylamine3×HCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 19890937HCID 19890937, compound

Product 1

HCID 19890958HCID 19890958, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

To a solution of 7 g (0.024 mol) 2-(2-picolylseleno)benzoic acid (from Example 1) and 2.4 g (0.024 mol) triethylamine in 40 ml dichloromethane which has been cooled to 0°-5° C. is added 6 g (0.024 mol) bis(2-oxo-3-oxazolidinyl)phosphoryl chloride in solid form as one portion. After stirring for 20 minutes a solution of 2.2 g (0.024 mol) aniline in 5 ml dichloromethane and a solution of 2.4 g (0.024 mol) triethylamine in 5 ml dichloromethane and a solution of 2.4 g (0.024 mol) triethylamine in 5 ml dichloromethane are added dropwise within 5 min, after 16 h at room temperature the reaction mixture is washed with 100 ml water. The organic phase is extracted successively with 100 ml 10% NaHCO3 solution, 100 ml 10% citric acid and 100 ml water. The organic phase is dried over sodium sulfate and the solvent removed under water pump vacuum. The solid crude product (6.3 g) is recrystallized from 35 ml 2-propanol.

Workup

  1. washis washed with 100 ml water
  2. extractionThe organic phase is extracted successively with 100 ml 10% NaHCO3 solution, 100 ml 10% citric acid and 100 ml water
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customthe solvent removed under water
  5. customThe solid crude product (6.3 g) is recrystallized from 35 ml 2-propanol

Sources & evidence

ORD record
ord-da697390857141a2b50b3e608161131f
Source dataset
uspto-grants-1992_06
Patent number
US05126357

Reaction notes

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