Dimethylformamide → HCID 22799976, compound

HRID 1438730Notes

Reaction equation

HRID 1438730 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[O:6][C@H:7]([C:16]([OH:18])=O)[O:8][C@H:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:4]=2[CH:3]=1.CN(C)C=O.S(Cl)(Cl)=O.[NH2:30][CH:31]([CH3:33])[CH3:32]>C(Cl)Cl>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[O:6][C@H:7]([C:16]([NH:30][CH:31]([CH3:33])[CH3:32])=[O:18])[O:8][C@H:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6363IsopropylamineHCID 24386Thionyl ChlorideHCID 12812406HCID 12812406, compound

Product 1

HCID 22799976HCID 22799976, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution at room temperature of 6.0 g (20.6 mmoles) of cis-6-chloro-4-phenyl-1,3-benzodioxan-2-carboxylic acid and ca. 1 ml of anhydrous DMF (dimethylformamide) in 300 ml of anhydrous CH2Cl2 was added dropwise a solution of 8.95 ml (123.6 mmoles) of thionyl chloride in 50 ml of anhydrous CH2Cl2. After addition, the solution was stirred and refluxed for 2.5 hours. The solvent and excess SOCl2 were then removed under reduced pressure and the residue was flashed down twice with anhydrous benzene to remove traces of SOCl2. The residue was redissolved in ca. 200 ml of CH2Cl2 and a solution of 7.7 g (130 mmoles) of 2-aminopropane in ca. 50 ml of CH2Cl2 was added. Heat was evolved. The solution was mixed well and allowed to stand in a stoppered flask at room temperature for 65 hours.

Workup

  1. additionAfter addition
  2. temperaturerefluxed for 2.5 hours
  3. customThe solvent and excess SOCl2 were then removed under reduced pressure
  4. customto remove traces of SOCl2
  5. dissolutionThe residue was redissolved in ca. 200 ml of CH2Cl2
  6. temperatureHeat
  7. additionThe solution was mixed well

Sources & evidence

ORD record
ord-398e15e09cfc4e3b9e6cf1b6afab5e4e
Source dataset
uspto-grants-1977_11
Patent number
US04056540

Reaction notes

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