Sulfuric Acid → HCID 24900991, compound

HRID 1158752Notes

Reaction equation

HRID 1158752 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[C:8]([C:25]([NH2:27])=[O:26])=[CH:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([CH2:19][C:20](O)([CH3:22])[CH3:21])[C:11]=2[N:24]=1.[OH-].[Na+].C(=O)(O)[O-:31].[Na+].[Cl:35][CH2:36][C:37]#[N:38]>O>[NH2:6][C:7]1[C:8]([C:25]([NH2:27])=[O:26])=[CH:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([CH2:19][C:20]([NH:38][C:37](=[O:31])[CH2:36][Cl:35])([CH3:21])[CH3:22])[C:11]=2[N:24]=1

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 7856ChloroacetonitrileHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 24900869HCID 24900869, compound

Product 1

HCID 24900991HCID 24900991, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Concentrated sulfuric acid (1.0 mL) was added dropwise to a solution of 43 (120 mg, 0.102 mmol) in chloroacetonitrile (1.0 mL) at 0° C. Stirring continued at this temperature for 1 h, then the reaction was diluted with water (5 mL) and the pH adjusted to 8-9 with 1N sodium hydroxide then aqueous saturated sodium bicarbonate. The aqueous phase was extracted with ethyl acetate (50 mL×3) then the combined organic phases were dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography (5-10% methanol in methylene chloride gradient) to afford the title compound (56, 120 mg, 80%). NH4OAc standard conditions. DAD Retention time =6.59 min. M+H=374. 1H NMR (300 MHz, CDCl3): Δ 8.39 (br s, 1H), 8.27 (s, 1H), 7.80 (d, J=7.3 Hz, 1H), 7.36-7.34 (m, 2H), 7.22 (dd, J=7.3, 7.3 Hz, 1H), 6.83 (br s, 2H), 5.80 (br s, 2H), 4.28 (s, 2H), 3.87 (s, 2H), 1.55 (s, 6H).

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate (50 mL×3)
  2. dry with materialthe combined organic phases were dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel chromatography (5-10% methanol in methylene chloride gradient)

Sources & evidence

ORD record
ord-66217190400b4344a535e7cb6cf2db76
Source dataset
uspto-grants-2010_10
Patent number
US07812018B2

Reaction notes

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