Diethyl Ether → 3-tert-Butoxycarbonyl-6-carbamimidoylthiomethyl-7-chloro-2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochloride

HRID 1670533Notes

Reaction equation

HRID 1670533 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([CH2:20]Cl)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:22][C:23]([NH2:25])=[S:24].CCOCC>O1CCOCC1>[ClH:19].[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([CH2:20][S:24][C:23](=[NH:22])[NH2:25])=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 2723790ThioureaHCID 597874103-tert-Butoxycarbonyl-7-chloro-6-chloromethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 673354473-tert-Butoxycarbonyl-6-carbamimidoylthiomethyl-7-chloro-2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochlorideYield 170.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 3-tert-butoxycarbonyl-7-chloro-6-chloromethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.742 g, 2.247 mmol) in anhydrous dioxane (9.4 mL) add thiourea (0.17 g, 2.2 mmol) at room temperature. Heat the mixture at 95° C. overnight. Cool the mixture to room temperature and add anhydrous ether (25 mL). Stir the mixture for 1 h and filter the slurry. Wash the solid with ether (25 mL) and dry to afford the desired intermediate as a white solid (0.780 g, 85%). MS (ES+) m/z: 370.2 (M+H)+.

Workup

  1. temperatureCool the mixture to room temperature
  2. filtrationfilter the slurry
  3. washWash the solid with ether (25 mL)
  4. customdry

Sources & evidence

ORD record
ord-db68d56c58614ec884688a597a995838
Source dataset
uspto-grants-2011_08
Patent number
US07994163B2

Reaction notes

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