Pyridine → 3-acetoxy-3-(N-acetylisopropylaminomethyl)-7-carbethoxyamino-3,4-dihydro-2H-1,5-benzodioxepin

HRID 267776Notes

Reaction equation

HRID 267776 reaction equation
[C:1]([O:4][C:5]1([CH2:17][N:18]([CH:22]([CH3:24])[CH3:23])[C:19](=[O:21])[CH3:20])[CH2:11][O:10][C:9]2[CH:12]=[CH:13][C:14]([NH2:16])=[CH:15][C:8]=2[O:7][CH2:6]1)(=[O:3])[CH3:2].Cl[C:26]([O:28][CH2:29][CH3:30])=[O:27].N1C=CC=CC=1>C(Cl)(Cl)Cl.O>[C:1]([O:4][C:5]1([CH2:17][N:18]([CH:22]([CH3:24])[CH3:23])[C:19](=[O:21])[CH3:20])[CH2:11][O:10][C:9]2[CH:12]=[CH:13][C:14]([NH:16][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:15][C:8]=2[O:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 540731773-acetoxy-3-(N-acetylisopropylaminomethyl)-7-amino-3,4-dihydro-2H-1,5-benzodioxepin

Product 1

HCID 538213713-acetoxy-3-(N-acetylisopropylaminomethyl)-7-carbethoxyamino-3,4-dihydro-2H-1,5-benzodioxepin

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

3-Acetoxy-3-N-acetylisopropylaminomethyl-7-amino-3,4-dihydro-2H-1,5-benzodioxepin (0.1 mole) from Example 86, Step B, in chloroform is treated with 0.11 mole of ethyl chloroformate and pyridine in chloroform. The mixture after stirring and heating in a water bath for several hours is diluted with water, extracted with ether, the combined ethereal extracts washed, dried and evaporated to give 3-acetoxy-3-(N-acetylisopropylaminomethyl)-7-carbethoxyamino-3,4-dihydro-2H-1,5-benzodioxepin.

Workup

  1. temperatureheating in a water bath for several hours
  2. extractionextracted with ether
  3. washthe combined ethereal extracts washed
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-6c8803a3d3b2481dac31f188b3ca1da3
Source dataset
uspto-grants-1976_03
Patent number
US03944560

Reaction notes

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