Thionyl Chloride → 5-(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yloxy)-pyrazine-2-carbonyl chloride

HRID 222692Notes

Reaction equation

HRID 222692 reaction equation
S(Cl)([Cl:3])=O.[CH:5]1([N:9]2[CH2:15][CH2:14][C:13]3[CH:16]=[C:17]([O:20][C:21]4[N:22]=[CH:23][C:24]([C:27]([OH:29])=O)=[N:25][CH:26]=4)[CH:18]=[CH:19][C:12]=3[CH2:11][CH2:10]2)[CH2:8][CH2:7][CH2:6]1>C1(C)C=CC=CC=1>[CH:5]1([N:9]2[CH2:15][CH2:14][C:13]3[CH:16]=[C:17]([O:20][C:21]4[N:22]=[CH:23][C:24]([C:27]([Cl:3])=[O:29])=[N:25][CH:26]=4)[CH:18]=[CH:19][C:12]=3[CH2:11][CH2:10]2)[CH2:8][CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 103151365-(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yloxy)-pyrazine-2-carboxylic acid

Product 1

HCID 866032205-(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yloxy)-pyrazine-2-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thionyl chloride (5 ml) was added slowly to 5-(3-cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yloxy)-pyrazine-2-carboxylic acid (E123a) (485 mg). The resulting reaction mixture was stirred at room temperature for 1 hour and then heated at reflux for a further 1 hour. The reaction mixture was cooled, diluted with toluene and concentrated in vacuo to afford the title compound which was used without further characterisation.

Workup

  1. customThe resulting reaction mixture
  2. temperatureheated
  3. temperatureat reflux for a further 1 hour
  4. temperatureThe reaction mixture was cooled
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-910bf7b0a27b4994b40cb5378f2f168d
Source dataset
uspto-grants-2012_06
Patent number
US08207331B2

Reaction notes

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