Hydrochloric Acid → HCID 178497398, compound

HRID 2240083Notes

Reaction equation

HRID 2240083 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([CH2:11][S:12]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:5]=1.Cl.[N:27]([O-])=O.[Na+].C(=O)(O)[O-].[Na+]>C1COCC1.O>[CH3:1][O:2][C:3]([C:4]1[CH:5]=[C:6]2[C:7](=[CH:8][CH:9]=1)[NH:10][N:27]=[C:11]2[S:12]([C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1)(=[O:13])=[O:14])=[O:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 68677983HCID 68677983, compound

Product 1

HCID 178497398HCID 178497398, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
3 °C

Procedure

A mixture of 4-amino-3-(naphthalene-1-sulfonylmethyl)benzoic acid methyl ester (0.9 g, 2.5 mmoles) in THF (5 mL), and 4M HCl (10 mL) was stirred in a round bottom flask, under nitrogen, at 3° C. A solution of sodium nitrite (0.18 g, 2.62 mmoles) in H2O (1 mL) was added dropwise. The reaction mixture was poured into a cold solution of saturated sodium bicarbonate (100 mL) and extracted with EtOAc. Compound was dried over Na2SO4, and concentrated under vacuum to afford the title compound as an off white solid (0.82 g, 2.25 mmoles).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialCompound was dried over Na2SO4
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-df6565d122cd454a89f5e47ee9f4f96f
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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