Hydrochloric Acid → HCID 71230796, compound

HRID 2199571Notes

Reaction equation

HRID 2199571 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]2[S:11][C:10]([C:12]3[S:13][C:14]([C:17]4[S:18][C:19]([C:27]5[S:28][C:29]([Br:32])=[CH:30][CH:31]=5)=[CH:20][C:21]=4[CH2:22][C:23]([O:25]C)=[O:24])=[CH:15][CH:16]=3)=[C:9]([CH2:33][C:34]([O:36]C)=[O:35])[CH:8]=2)=[CH:4][CH:3]=1.[OH-].[Na+].O.Cl>O1CCOCC1>[Br:32][C:29]1[S:28][C:27]([C:19]2[S:18][C:17]([C:14]3[S:13][C:12]([C:10]4[S:11][C:7]([C:5]5[S:6][C:2]([Br:1])=[CH:3][CH:4]=5)=[CH:8][C:9]=4[CH2:33][C:34]([OH:36])=[O:35])=[CH:16][CH:15]=3)=[C:21]([CH2:22][C:23]([OH:25])=[O:24])[CH:20]=2)=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium Hydroxide2×HCID 56839264HCID 56839264, compound

Product 1

HCID 71230796HCID 71230796, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
80 °C

Procedure

Intermediate O (707 mg, 0.989 mmol) was dissolved in dioxane (5 ml) and 2 M NaOH (5 ml) was added. The mixture was heated at 80° C. for 1 h and dioxane (10 ml) and 2 M NaOH (10 ml) was added. The mixture was stirred for 1 h at 80° C. Water was added and the mixture acidified using 6 M HCl. The precipitated material was isolated by centrifugation, washed with water and dried at high vacuum overnight. Yield: 679 mg (100%); orange solid. 1H NMR (400 MHz, DMSO-d6): δ 3.75 (s, 4H), 7.21 (d, J 3.8 Hz, 2H), 7.25 (d, J 3.8 Hz, 2H), 7.29 (s, 2H), 7.31 (s, 2H),

Workup

  1. customThe precipitated material was isolated by centrifugation
  2. washwashed with water
  3. customdried at high vacuum overnight

Sources & evidence

ORD record
ord-6a9e8b21f8744da096e5538a22de310d
Source dataset
uspto-grants-2016_06
Patent number
US09359311B2

Reaction notes

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