Hydrochloric Acid → HCID 60209020, compound

HRID 1476193Notes

Reaction equation

HRID 1476193 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[O:9][C:10]3[C:15]([C:16](=[O:24])[C:17]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:3][CH2:2]1.[ClH:25]>C1COCC1.C(OCC)C>[ClH:25].[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[O:9][C:10]3[C:15]([C:16](=[O:24])[C:17]=2[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58269245HCID 58269245, compound

Product 1

HCID 60209020HCID 60209020, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 4 (0.065 g, 0.202 mmoles) in THF (2 ml), was added hydrochloric acid in diethyl ether (2 ml) at 0° C. and stirred for 30 min. The precipitate formed was filtered, washed with pentane and dried to afford the title compound as off-white solid (0.043 g, 60% yield. MP: 208-209° C. 1H-NMR (δ ppm, DMSO-D6, 400 MHz): δ 11.42(br s, 1H), 8.08(d, J=7.8 Hz, 1H), 7.90 (t, J=8.1 Hz, 1H), 7.79(d, J=8.4Hz, 1H), 7.55(t, J=7.5Hz,1H), 7.49-7.44(m,3H), 7.33(d, J=7.3Hz,2H), 4.24(br s, 2H), 3.81(br s, 5H), 3.08(br s, 3H). 322.10(M++1-HCl).

Workup

  1. customThe precipitate formed
  2. filtrationwas filtered
  3. washwashed with pentane
  4. customdried

Sources & evidence

ORD record
ord-8b251456d09b40a081ab16adbef47fbc
Source dataset
uspto-grants-2015_04
Patent number
US09018375B2

Reaction notes

Loading…