Benzyl Bromide → HCID 54562563, compound

HRID 1633057Notes

Reaction equation

HRID 1633057 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([O:11][C:12]([N:14]1[CH2:24][CH2:23][C:17]2[N:18]=[N:19][C:20]([SH:22])=[CH:21][C:16]=2[CH2:15]1)=[O:13])[CH3:10].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:9]([O:11][C:12]([N:14]1[CH2:24][CH2:23][C:17]2[N:18]=[N:19][C:20]([S:22][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:21][C:16]=2[CH2:15]1)=[O:13])[CH3:10]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178473320HCID 178473320, compound

Product 1

HCID 54562563HCID 54562563, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 13.2 g of benzyl bromide in 75 cc of dimethyl formamide is added dropwise within 2 hours to a suspension heated to 50° of 18.5 g of 5,6,7,8-tetrahydro-3-mercapto-6-pyrido[4,3-c]pyridazinecarboxylic acid ethyl ester and 12.8 g of potassium carbonate in 200 cc of dimethyl formamide. The mixture is subsequently stirred at the same temperature for 20 hours and is then completely concentrated in a vacuum. The residue is divided between 200 cc of chloroform and 50 cc of water, the organic phase is separated and concentrated to a dark oil in a vacuum. This is chromatographed on an aluminum oxide column, and elution is effected with a mixture of benzene/petroleum ether 2:1. The crude oily 3-benzylmercapto-5,6,7,8-tetrahydro-6-pyrido[4,3-c]pyridazinecarboxylic acid ethyl ester, obtained after concentrating the eluate, crystallizes from 75 cc of ether after the addition of 25 cc of petroleum ether.

Workup

  1. additionis added dropwise within 2 hours to a suspension
  2. concentrationis then completely concentrated in a vacuum
  3. customthe organic phase is separated
  4. concentrationconcentrated to a dark oil in a vacuum
  5. customThis is chromatographed on an aluminum oxide column, and elution
  6. additionis effected with a mixture of benzene/petroleum ether 2:1

Sources & evidence

ORD record
ord-98a992cf41be4459958ff7ab76c378cf
Source dataset
uspto-grants-1984_10
Patent number
US04478837

Reaction notes

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