Picolyl chloride hydrochloride → HCID 66706646, compound

HRID 911483Notes

Reaction equation

HRID 911483 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([S:20][C:21](N(C)C)=O)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.[N:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1CCl>C(OCC)C>[ClH:19].[Cl:19][C:16]1[CH:17]=[CH:18][C:11]2[CH2:10][CH2:9][NH:8][CH2:14][CH2:13][C:12]=2[C:15]=1[S:20][CH2:21][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][N:27]=1

Participants

4

Reactant 2

HCID 23392Picolyl chloride hydrochlorideHCID 576559793-tert-butoxycarbonyl-7-chloro-6-dimethylaminocarbonylthio-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 66706646HCID 66706646, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Using a method similar to the General Procedure 7, react 3-tert-butoxycarbonyl-7-chloro-6-dimethylaminocarbonylthio-2,3,4,5-tetrahydro-1H-benzo[d]azepine (8 g, 20.8 mmol) with 2-picolyl chloride hydrochloride (3.41 g, 20.8 mmol). Dilute the reaction mixture with diethyl ether and filter the precipitate. Concentrate the filtrate in vacuo, dissolve the residue in diethyl ether (100 mL) and add 1N aqueous HCl (100 mL). Stir the mixture for 16 h at ambient temperature. Separate, wash the aqueous layer with diethyl ether, adjust the pH of the aqueous layer to 12 with sodium hydroxide and extract with diethyl ether. Dry over Na2SO4 and concentrate in vacuo to give the free base of the title compound. Use the General Procedure 2-2 to give the title compound as a white solid (4.91 g, 78%). MS (ES+) m/z: 305 (M+H)+.

Workup

  1. filtrationfilter the precipitate
  2. concentrationConcentrate the filtrate in vacuo
  3. dissolutiondissolve the residue in diethyl ether (100 mL)
  4. additionadd 1N aqueous HCl (100 mL)
  5. customSeparate
  6. washwash the aqueous layer with diethyl ether
  7. extractionextract with diethyl ether
  8. dry with materialDry over Na2SO4
  9. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-f92c65fd8e9b4847ac15f347490ffe5e
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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