Hydrochloric Acid → HCID 29548813, compound
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+].COC(O)C.Cl.C(=O)([O-])[O-].[Na+].[Na+]>O>[NH2:1][C:4]1[CH:5]=[C:6]([S:10]([NH:13][CH2:14][C:15]2[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1Participants
Conditions
- Temperature
- 70 °C
Procedure
A mixture of 3-nitro-N-(pyridin-4-ylmethyl)-benzenesulfonamide [CAS No. 332942-34-4, commercially available] (1.23 g, 4.2 mmol), sodium dithionite (3.09 g, 15.1 mmol), water (10 ml) and 2 methoxyethanol (10 ml) was stirred at 100° C. for 2 h, additional water (7 ml) was added at 70° C. and subsequently HCl (37%, 7 ml) was added over a period of 10 min (SO2 evolution). The reaction mixture was stirred at 70° C. for 20 min, poured into ice/water (50 ml) and sodium carbonate was added until the solution proofed to be basic. The solution was extracted with ethyl acetate/MeOH 9:1 (3×75 ml), the combined organic layers washed with brine (80 ml), dried (MgSO4) and evaporated. The crude product was further purified by column chromatography on silica gel (MeOH/ethyl acetate 1:9) to yield the title compound (0.8 g, 72%) as a light yellow solid. MS (ISP) 261.9 [(M−H)−]; m.p. 139° C.
Workup
- additionwas added until the solution
- extractionThe solution was extracted with ethyl acetate/MeOH 9:1 (3×75 ml)
- washthe combined organic layers washed with brine (80 ml)
- dry with materialdried (MgSO4)
- customevaporated
- customThe crude product was further purified by column chromatography on silica gel (MeOH/ethyl acetate 1:9)
Sources & evidence
- ORD record
- ord-4f25360f2f0a4f669edd2c8092dc8c5b
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07378417B2
Reaction notes
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