Hydrochloric Acid → HCID 60209019, compound

HRID 1484324Notes

Reaction equation

HRID 1484324 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([CH2:12][N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[C:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:5]2=[O:25].[ClH:26]>C1COCC1.C(OCC)C>[ClH:26].[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([CH2:12][N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[C:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:5]2=[O:25]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58269171HCID 58269171, compound

Product 1

HCID 60209019HCID 60209019, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 2 (0.10 g, 0.249 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 pale yellow solid (0.110 g, 99% yield. MP: 229-230° C. 1H-NMR (δ ppm, DMSO-D6, 400 MHz): δ 8.13 (s, 1H), 8.06 (d, J=8.7 Hz, 1H), 7.77 (d, J=8.8 Hz, 1H), 7.48 (m, 3H), 7.32 (d, J=6.9 Hz, 2H), 4.35 (br s, 2H), 3.80 (br s, 4H), 3.59 (s, 2H), 3.25 (br s, 2H). Mass: 402.04 (M++1-HCl).

Workup

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

Sources & evidence

ORD record
ord-32399d1e33554d73beedc67e1470ce45
Source dataset
uspto-grants-2016_08
Patent number
US09421209B2

Reaction notes

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