Iodine → HCID 13467419, compound

HRID 1065608Notes

Reaction equation

CO[C:3]1[CH:4]=[C:5](CC)[C:6]([NH:9][C:10](=O)[CH3:11])=[CH:7][CH:8]=1.Br[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:22](=O)([O-])[O-:23].[K+].[K+].II>[Cu]>[CH3:22][O:23][C:16]1[CH:17]=[CH:18][C:19]([CH2:11][CH2:10][NH:9][C:6]2[CH:7]=[CH:8][CH:3]=[CH:4][CH:5]=2)=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 200 °C

Procedure

19.3 g. of 3-methoxy-6-acetylamino-1-ethylbenzene, 22 g. of bromobenzene, 7.78 g. of potassium carbonate, 0.43 g. of copper powder and 0.01 g. of iodine were refluxed under ordinary pressure for 48 hours on the oil bath. Then excess bromobenzene was recovered by means of steam distillation, and the remaining solid [crude 3-methoxy-6(N-acetylanilino)ethylbenzene] was filtered off, mixed, without purifying, with 140 ml. of a 10 percent aqueous solution of caustic soda and heated in the autoclave to 200° C. for 8 hours. After cooling, an oil layer was separated from it and purified by means of distillation under reduced pressure. Then 14.8 g. (66.0 percent of theoretical) of 3-methoxy-6-anilinoethylbenzene was obtained as a light yellow oily substance having a boiling point of 185° to 215° C./13 mmHg, and the formula: ##STR16##

Workup

distillationThen excess bromobenzene was recovered by means of steam distillation
filtrationthe remaining solid [crude 3-methoxy-6(N-acetylanilino)ethylbenzene] was filtered off
additionmixed
customwithout purifying, with 140 ml
temperatureAfter cooling
customan oil layer was separated from it
distillationpurified by means of distillation under reduced pressure

Sources & evidence

ORD record: ord-2a4c8794acae4f7b80ae28636a798b70
Source dataset: uspto-grants-1982_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04330473

Reaction notes

Loading…