Water → HCID 69835226, compound

HRID 1870253Notes

Reaction equation

HRID 1870253 reaction equation
C([CH:4]=[C:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:8][CH2:7][CH2:6]1)(O)=O.[CH:26]([NH2:29])([CH3:28])[CH3:27].P(C#N)(OCC)(OCC)=[O:31].O>CN(C)C=O>[CH:26]([O:31][CH:24]([CH3:23])[CH3:19])([CH3:28])[CH3:27].[CH:26]([NH:29][CH:4]=[C:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([S:16]([C:19]2[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=2)(=[O:17])=[O:18])[CH2:8][CH2:7][CH2:6]1)([CH3:28])[CH3:27]

Participants

7

Reactant 4

HCID 962WaterHCID 6363IsopropylamineHCID 76257Diethyl cyanophosphonateHCID 54287519HCID 54287519, compound

Product 2

HCID 7914Diisopropyl EtherHCID 69835226HCID 69835226, compoundYield 205.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-carboxymethylidene-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-benzazepine (3.0 g) and isopropylamine (2.5 g) in dimethylformamide (30 ml) is added diethyl cyanophosphate (2.1 g), and the mixture is stirred at room temperature for 30 minutes. To the mixture is added water, and the mixture is extracted with ethyl acetate. The extract is washed with water, dried, concentrated, and the precipitated crystals are recrystallized from chloroform--diisopropyl ether to give 5-isopropylaminomethylidene-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-benzazepine (trans-compound) (3.2 g).

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe extract is washed with water
  3. customdried
  4. concentrationconcentrated
  5. customthe precipitated crystals are recrystallized from chloroform

Sources & evidence

ORD record
ord-2ec03966853b47afa562e839d5a915b8
Source dataset
uspto-grants-2000_08
Patent number
US06096736

Reaction notes

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