Hydrochloric Acid → HCID 57710193, compound

HRID 1099535Notes

Reaction equation

HRID 1099535 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Mg].BrC(Br)C.[O:14]1[CH2:18][CH2:17][NH:16]C1.Cl.[CH2:20]1[CH2:24][O:23][CH2:22][CH2:21]1>C1(C)C=CC=CC=1.II>[OH:14][CH2:18][CH2:17][N:16]1[CH2:20][CH2:24][O:23][CH2:22][CH:21]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 112011,1-DibromoethaneHCID 123691-BromoheptaneHCID 5366831,3-OxazolidineHCID 5462224Magnesium

Product 1

HCID 57710193HCID 57710193, compound

Reagents, catalysts & solvents 2

HCID 807IodineCatalystHCID 1140TolueneSolvent2×

Procedure

200 g of 1-Bromoheptane were slowly added at 65° C. to a suspension of 32.6 g of magnesium, 0.5 g of iodine and 2.4 ml of Dibromoetane in a mixture of 182 ml of THF and 400 ml of toluene. The reaction mixture was stirred at the same temperature for 3 h. When the formation of the corresponding Grignard compound was completed, the mixture was cooled down at room temperature and a solution of 158 g of Oxazolidine (II) in 500 ml of toluene was added in 1 hour. The mixture was stirred for 30 min. and then added to 795 ml solution of aqueous 5% HCl. The organic layer is decanted and concentrated until dryness. Compound (IC) was obtained as an orange oil (179 g). MS (EI), (m/z, %): 229 (M+., 1), 198 (M-CH2OH, 25). 130 (M-C7H15, 100), 112 (M-C7H15-H2O, 4), 100 (M-73, 30), 85 (5 56 (10), 41 (8).

Workup

  1. stirringThe mixture was stirred for 30 min.
  2. customThe organic layer is decanted
  3. concentrationconcentrated until dryness

Sources & evidence

ORD record
ord-69461c60e6314adcadf600e8fbc06cb2
Source dataset
uspto-grants-2012_03
Patent number
US08143463B2

Reaction notes

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