Sodium Dithionite → 4-(Cyclopropylmethyl-amino)-benzenesulfonic acid 3,4-diamino-phenyl ester

HRID 1823781Notes

Reaction equation

HRID 1823781 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([NH:26][CH2:27][CH:28]3[CH2:30][CH2:29]3)=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[CH:12][C:11]=1[N+:31]([O-])=O.[Na]>C(O)C>[NH2:31][C:11]1[CH:12]=[C:13]([O:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([NH:26][CH2:27][CH:28]3[CH2:29][CH2:30]3)=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH:14]=[CH:15][C:10]=1[NH2:9]

Participants

5

Reactant 3

HCID 24489Sodium DithioniteHCID 5360545SodiumHCID 865960784-(Cyclopropylmethyl-amino)-benzenesulfonic acid 4-amino-3-nitro-phenyl ester

Product 1

HCID 865960794-(Cyclopropylmethyl-amino)-benzenesulfonic acid 3,4-diamino-phenyl esterYield 90.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Sodium dithionite (3 g) was added to a solution of 4-(cyclopropylmethyl-amino)-benzenesulfonic acid 4-amino-3-nitro-phenyl ester (783 mg) and sodium hydroxyde (0.5 N, 15 ml) in ethanol (30 ml) at 80° C. The reaction mixture was stirred at 80° C. for 10 minutes then filtered then the filtrate was evaporated. The residue was extracted three times with ethyl acetate (30 ml). The combined extracts were dried over magnesium sulfate then evaporated to give 652 mg of 4-(cyclopropylmethyl-amino)-benzenesulfonic acid 3,4-diamino-phenyl ester.

Workup

  1. filtrationthen filtered
  2. customthe filtrate was evaporated
  3. extractionThe residue was extracted three times with ethyl acetate (30 ml)
  4. dry with materialThe combined extracts were dried over magnesium sulfate
  5. customthen evaporated

Sources & evidence

ORD record
ord-f49c417d71884c3faacbe21f3670e29d
Source dataset
uspto-grants-2006_05
Patent number
US07041668B2

Reaction notes

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