Thionyl Chloride → benzyl 5-(chloromethyl)-2,3-dihydro-1H-inden-1-ylcarbamate

HRID 473097Notes

Reaction equation

HRID 473097 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH:12]([NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:11][CH2:10]2>C(Cl)Cl>[Cl:3][CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH:12]([NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:11][CH2:10]2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 67088218Benzyl 5-(hydroxymethyl)-2,3-dihydro-1H-inden-1-ylcarbamate

Product 1

HCID 70220201benzyl 5-(chloromethyl)-2,3-dihydro-1H-inden-1-ylcarbamateYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (2.0 g, 16.8 mmol) was added to a suspension of benzyl 5-(hydroxymethyl)-2,3-dihydro-1H-inden-1-ylcarbamate (2.53 g, 8.5 mmol) in DCM (35 mL). The solution was stirred at rt for 1 h before the reaction mixture was evaporated to dryness in vacuo and the material was co-evaporated with diethyl ether (2×100 mL) to afford the title compound as a white solid (2.63 g, 98%). MS (ESI): m/z [M+NH4]+ 333.2

Workup

  1. customwas evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-f7b4be6e6c64421b8a22a9b4a2ce8298
Source dataset
uspto-grants-2014_01
Patent number
US08633237B2

Reaction notes

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