4-Methoxybenzylamine → HCID 22139400, compound

HRID 1825790Notes

Reaction equation

HRID 1825790 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[CH2:11]([O:18][C:19]1[C:32]2[S:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24](=[O:33])[C:23]=2[C:22](F)=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>N1C=CC=CC=1>[CH2:11]([O:18][C:19]1[C:32]2[S:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24](=[O:33])[C:23]=2[C:22]([NH:8][CH2:7][C:6]2[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 22139411HCID 22139411, compound

Product 1

HCID 22139400HCID 22139400, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 4-methoxybenzyl amine (1.63 g, 11.89 mmol) in dry pyridine (10 ml) was added 4-Benzyloxy-1-fluoro-thioxanthen-9-one (1 g, 2.97 mmol) in a single portion. The mixture was then heated to reflux (140° C.) for 18 hrs. The resulting hot orange suspension was allowed to cool to room temperature before being poured onto 100 ml of crushed ice. The precipitate was filtered off and washed with copious amounts of water to give the title compound as a red/orange solid (1.35 g, 89.6%). m/z (LC-MS, ESP): 454 [M+H]+ R/T=6.09 mins.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto cool to room temperature
  3. filtrationThe precipitate was filtered off
  4. washwashed with copious amounts of water

Sources & evidence

ORD record
ord-451fd55079754f3dbc7b853bbafdb017
Source dataset
uspto-grants-2006_05
Patent number
US07049313B2

Reaction notes

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