Lawesson's reagent → HCID 57656515, compound

HRID 911733Notes

Reaction equation

HRID 911733 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH2:10][C:4]=2[C:3]=1[S:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=O)[NH:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:17][CH:16]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:37]2)=CC=1>O1CCOCC1>[Cl:1][C:2]1[CH:12]=[CH:11][C:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH2:10][C:4]=2[C:3]=1[S:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[S:37])[NH:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 66706921HCID 66706921, compound

Product 1

HCID 57656515HCID 57656515, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Combine 7-chloro-6-(4-tert-butylcarbamoyl-benzylthio)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (53 mg, 0.13 mmol) with 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (Lawesson's reagent) (53 mg, 0.13 mmol) in anhydrous 1,4-dioxane (1 mL) in a sealed tube and heat at 100° C. for 2 h. Cool the reaction mixture to room temperature, concentrate in vacuo and purify the residue by SCX chromatography to obtain 7-chloro-6-(4-tert-butylthiocarbamoyl-benzylthio)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a yellow oil. Purify by reverse phase preparative HPLC [Zorbax SB-Phenyl 21.2×250 mm, 5 micron, 22 mL/min of 0.1% aqueous HCl/acetonitrile (9:1 to 1:9) over 30 min, detector at 230 nm].

Workup

  1. concentrationconcentrate in vacuo
  2. custompurify the residue by SCX chromatography

Sources & evidence

ORD record
ord-d17ad8f5f460495d9c03538861dfc4b2
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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