Hydrogen Bromide → N-((S)-3-bromo-2-hydroxypropyl)-5-chlorothiophene-2-carboxamide

HRID 425235Notes

Reaction equation

[BrH:1].[OH:2][C@H:3]([CH2:14]O)[CH2:4][NH:5][C:6]([C:8]1[S:9][C:10]([Cl:13])=[CH:11][CH:12]=1)=[O:7].C(OC(=O)C)(=O)C.CO>C(O)(=O)C>[Br:1][CH2:14][C@@H:3]([OH:2])[CH2:4][NH:5][C:6]([C:8]1[S:9][C:10]([Cl:13])=[CH:11][CH:12]=1)=[O:7]

Participants

Conditions

Temperature: 62.5 °C

Procedure

301.7 ml of a 33% solution of hydrobromic acid in acetic acid are added to a suspension of 100 g of N-((S)-2,3-dihydroxypropyl)-5-chlorothiophene-2-carboxamide (VIII) in 250 ml of glacial acetic acid at from 21 to 26° C. over a period of 30 minutes. Subsequently, 40 ml of acetic anhydride are added and the reaction mixture is stirred at from 60 to 65° C. for three hours. At 20 to 25° C., 960 ml of methanol are then added over a period of 30 minutes. The reaction mixture is stirred under reflux for 2.5 hours and then overnight at from 20 to 25° C. For workup, the solvents are distilled off under reduced pressure at approx. 95 mbar. The remaining suspension is admixed with 50 ml of 1-butanol and 350 ml of water. The precipitated product is filtered off with suction, washed with water and dried.

Workup

stirringThe reaction mixture is stirred
temperatureunder reflux for 2.5 hours
customovernight
customat from 20 to 25° C
distillationFor workup, the solvents are distilled off under reduced pressure at approx. 95 mbar
filtrationThe precipitated product is filtered off with suction
washwashed with water
customdried

Sources & evidence

ORD record: ord-2cc01475d2b741888dc6133267712869
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106192B2

Reaction notes

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