Sodium Bicarbonate → HCID 178519381, compound

HRID 2240086Notes

Reaction equation

HRID 2240086 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH2:10][S:11]([C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)(=[O:13])=[O:12].[N:24]([O-])=O.[Na+].C(=O)(O)[O-].[Na+]>C1COCC1.Cl.O>[C:14]1([S:11]([C:10]2[C:3]3[C:2](=[CH:9][CH:8]=[C:5]([CH:6]=[O:7])[CH:4]=3)[NH:1][N:24]=2)(=[O:13])=[O:12])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 86610770HCID 86610770, compound

Product 1

HCID 178519381HCID 178519381, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
3 °C

Procedure

A mixture of 4-amino-3-(naphthalene-1-sulfonylmethyl)-benzaldehyde (2.4 g, 6.85 mmoles) in THF (10 mL) and 4M HCl (20 mL) was stirred in a round bottom flask at 3° C. A solution of sodium nitrite (0.49 g, 7.19 mmoles in H2O (2 mL) was added. 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 (1.84 g, 5.5 mmoles).

Workup

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

Sources & evidence

ORD record
ord-093c47194ed54affaee6b0a409bee69f
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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