Dichloromethane → HCID 15053682, compound

HRID 1073733Notes

Reaction equation

HRID 1073733 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.ClCCl.[CH2:20]([O:22][P:23]([CH2:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1)([O:25][CH2:26][CH3:27])=[O:24])[CH3:21]>CN(C)C1C=CN=CC=1.ClC(Cl)C.O>[CH2:26]([O:25][P:23]([CH2:28][C:29]1[CH:30]=[CH:31][C:32]([C:33]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][CH2:2]2)=[O:34])=[CH:36][CH:37]=1)([O:22][CH2:20][CH3:21])=[O:24])[CH3:27]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 10328IndolineHCID 104469734-[(Diethoxyphosphoryl)-methyl]benzoyl chloride

Product 1

HCID 15053682HCID 15053682, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

1.80 Grams (15 mM) of indoline, 1.82 g (18 mM) of triethylamine and 0.37 g (3 mM) of 4-dimethylaminopyridine were dissolved in 30 ml of dry dichloroethane, to this solution was added dropwise slowly 30 ml of dry dichloromethane solution with 5.21 g (15 mM) of 4-diethoxyphosphinoylmethylbenzoyl chloride at 0° C. with stirring. After the stirring was continued for 10 hours at room temperature, 50 ml of water was added to the reaction mixture and extracted with chloroform. The extracts were dried over anhydrous sodium sulfate, and concentrated. The residue thus obtained was purified by means of a silica gel column chromatography (eluted with chloroform:ethyl acetate=1:1). The crude crystals were recrystallized from benzene-n-hexane to yield 3.90 g of 1-(4-diethoxyphosphinoylmethylbenzoyl)indoline as colorless crystals Melting point 93.0°-94.5° C.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe extracts were dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe residue thus obtained
  5. customwas purified by means of a silica gel column chromatography (eluted with chloroform:ethyl acetate=1:1)
  6. customThe crude crystals were recrystallized from benzene-n-hexane

Sources & evidence

ORD record
ord-12790a64000947c4be33f0ae15f25eec
Source dataset
uspto-grants-1990_11
Patent number
US04971957

Reaction notes

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