Thionyl Chloride → HCID 20402698, compound

HRID 1980261Notes

Reaction equation

HRID 1980261 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[C:10](=[CH:18][N:19]([CH3:22])[C:20]=2[CH3:21])[N:11]([CH3:17])[C:12](=[O:16])[CH:13](O)[N:14]=1.S(Cl)(Cl)=O.Cl.[CH2:28]([O:30][C:31](=[O:36])[CH2:32][CH2:33][CH2:34][NH2:35])[CH3:29]>C(N(CC)CC)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[C:10](=[CH:18][N:19]([CH3:22])[C:20]=2[CH3:21])[N:11]([CH3:17])[C:12](=[O:16])[CH:13]([NH:35][CH2:34][CH2:33][CH2:32][C:31]([O:30][CH2:28][CH3:29])=[O:36])[N:14]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 126496614-Aminobutyrate ethyl hydrochlorideHCID 20402684HCID 20402684, compound

Product 1

HCID 20402698HCID 20402698, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 5-(2-chlorophenyl)-1,7-dihydro-3-hydroxy-1,6,7-trimethyl-pyrrolo[3,4-e][1,4]diazepin-2(3H)-one (6.3 g, 0.0198 mole) and thionyl chloride (18 mole) is allowed to stand at room temperature for one night. The 3-chloro derivative which forms is precipitated by the addition of ethyl ether, recovered by filtration and washed on filter with ethyl ether. The obtained intermediate is dissolved in chloroform (100 ml) and triethylamine (8 g) and γ-aminobutyric acid ethyl ester hydrochloride (6.4 g, 0.0382 mole) are gradually added to the obtained solution. The reaction mixture is allowed to stand, at room temperature for one day, then chloroform is evaporated, the residue is taken up with water acidified with HCl and the undissolved oil is extracted with chloroform. The chloroform solution is neutralized by washing with aqueous NaHCO3, dried over Na2SO4, filtered and concentrated to dryness yielding 6 g of an oily residue.

Workup

  1. waitto stand at room temperature for one night
  2. customThe 3-chloro derivative which forms is precipitated by the addition of ethyl ether
  3. filtrationrecovered by filtration
  4. washwashed
  5. filtrationon filter with ethyl ether
  6. dissolutionThe obtained intermediate is dissolved in chloroform (100 ml)
  7. customchloroform is evaporated
  8. extractionthe undissolved oil is extracted with chloroform
  9. washby washing with aqueous NaHCO3
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-10b98399944e4b72b515c01ab7fbd767
Source dataset
uspto-grants-1985_04
Patent number
US04508730

Reaction notes

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