Hydrogen Bromide → HCID 70342591, compound

HRID 583128Notes

Reaction equation

HRID 583128 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([C:12]2[O:13][C:14](=[O:30])[N:15]([CH:17]3[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][C:26]([F:29])([F:28])[F:27])[CH2:19][CH2:18]3)[N:16]=2)[C:5]2[O:6][CH2:7][CH2:8][O:9][C:4]=2[C:3]=1[NH:31]C(=O)OCC1C=CC=CC=1.Br.C(OCC)C>C(O)(=O)C>[NH2:31][C:3]1[C:4]2[O:9][CH2:8][CH2:7][O:6][C:5]=2[C:10]([C:12]2[O:13][C:14](=[O:30])[N:15]([CH:17]3[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][C:26]([F:28])([F:27])[F:29])[CH2:19][CH2:18]3)[N:16]=2)=[CH:11][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 86754299HCID 86754299, compound

Product 1

HCID 70342591HCID 70342591, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

1.72 g (2.88 mmol) of phenylmethyl [6-chloro-8-[5-oxo-4-[1-(4,4,4-trifluorobutyl)piperidin-4-yl]-4,5-dihydro-1,3,4-oxadiazol-2-yl]-2,3-dihydro-1,4-benzodioxin-5-yl]carbamate and 17 ml of acetic acid are introduced into a 100 ml round-bottomed flask, 5 ml of 33% hydrobromic acid in acetic acid are added and the mixture is stirred at room temperature for 7 h. Diethyl ether is added to the precipitate which has formed and 1.8 g of hydrobromide are collected by filtration. It is taken up in water and chloroform, sodium hydroxide is added in order to release the base and, after the usual treatment of the organic phase, 1.19 g of compound are obtained. Melting point: 188° C.

Workup

  1. customhas formed
  2. filtration1.8 g of hydrobromide are collected by filtration
  3. additionchloroform, sodium hydroxide is added in order

Sources & evidence

ORD record
ord-2d2c8b820fd3444ba088e7fed66e119d
Source dataset
uspto-grants-1999_07
Patent number
US05929089

Reaction notes

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