Hydrochloric Acid → HCID 9883927, compound

HRID 1603229Notes

Reaction equation

HRID 1603229 reaction equation
[CH3:1][C@H:2]1[CH2:7][C:6]2[CH:8]=[C:9]3[O:14][CH2:13][O:12][C:10]3=[CH:11][C:5]=2[CH:4]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[O:3]1.CS(C)=[O:26].[OH-].[Na+].Cl>CN(C)C=O>[CH3:1][C@H:2]1[CH2:7][C:6]2[CH:8]=[C:9]3[O:14][CH2:13][O:12][C:10]3=[CH:11][C:5]=2[C:4]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)([OH:26])[O:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 10969017(5RS,7S)-7,8-dihydro-7-methyl-5-(4-nitrophenyl)-5H-1,3-dioxolo-[4,5-G][2]benzopyran

Product 1

HCID 9883927HCID 9883927, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

350 grams of the isomeric intermediate from Example 4 was added to a solution of 731 mL of dimethylsulfoxide and 2923 mL of dimethylformamide. The mixture was cooled to 8-12° C. and compressed air was passed through the mixture. 117.5 mL of 50% aqueous sodium hydroxide was added in one portion and the resulting mixture was stirred for 4.5 h. The reaction mixture was added by cannula over 30-60 min to 8.25 L of a stirred 1N hydrochloric acid solution at 10-15° C. The resulting precipitate was filtered and washed with 3 L of water then air dried to a constant weight (384 g). The wet cake was carried into Example 6 without further drying. P chem: Data recorded from a 3:1 isomeric mixture. TLC Rf =0.19 (75:25 hexane:ethyl acetate); IR (CHCl3) 3605, 3590, 3015, 3000, 2960, 2910, 1608, 1522, 1484, 1352, 1240, 1042cm-1 -; 1H NMR (CDCl3, 300 MHz) δ(major isomer) 8.16 (d, 2H, j=6.9 Hz), 7.73 (d, 2H, J=6.9 Hz), 6.55 (s, 1H), 6.38 (s, 1H), 5.86 (s, 1H), 5.83 (s, 1H), 4.38 (M, 1H), 2.70 (m, 2H), 1.39 (d, 3H, J=6.3 Hz); d (minor isomer) 8.27 (d, 2H, J=8.9 Hz), 7.90 (d, 2H, J=8.6 Hz), 6.87 (s, 1H), 6.73 (s, 1H), 6.03 (s, 1H), 6.02 (s, 1H), 3.95 (m, 1H), 2.7 (obscured, m, 2H), 1.24 (d, 3H, J=6.1 Hz); mass spectrum, m/z (FD, M+) 329; Anal. Calcd. for C17H15NO6 : C, 62.01; H, 4.59; N, 4.25. found C, 62.22, H, 4.79; N, 4.29.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with 3 L of water
  3. customair dried to a constant weight (384 g)

Sources & evidence

ORD record
ord-9253cd02b02c48f78b1674675b3e5659
Source dataset
uspto-grants-1999_11
Patent number
US05986114

Reaction notes

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