Sodium Dithionite → 2,3-Diamino-5-ethylsulfanyl-benzoic acid ethyl ester

HRID 1845102Notes

Reaction equation

HRID 1845102 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:10]=[C:9]([S:11][CH2:12][CH3:13])[CH:8]=[C:7]([NH2:14])[C:6]=1[N+:15]([O-])=O)[CH3:2].[O-]S(S([O-])=O)=O.[Na+].[Na+]>C(O)C.C(OCC)(=O)C.O>[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:10]=[C:9]([S:11][CH2:12][CH3:13])[CH:8]=[C:7]([NH2:14])[C:6]=1[NH2:15])[CH3:2]

Participants

4

Reactant 2

HCID 24489Sodium DithioniteHCID 669408103-Amino-5-ethylsulfanyl-2-nitro-benzoic acid ethyl ester

Product 1

HCID 669405052,3-Diamino-5-ethylsulfanyl-benzoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 86601158Ethanol ethyl acetate waterSolvent

Procedure

1.5 g (5.5 mmol) of 3-amino-5-ethylsulfanyl-2-nitro-benzoic acid ethyl ester was reduced by 2.9 g (16.6 mmol) of Na2S2O4 in 28 mL of ethanol/ethyl acetate/water (3:3:1) at 80° C. for 3 h to produce 2,3-diamino-5-ethylsulfanyl-benzoic acid ethyl ester. LCMS: 241 (M+1)+.

Sources & evidence

ORD record
ord-6e8414d023fe443fbbcbd9ca6d4c2f31
Source dataset
uspto-grants-2015_02
Patent number
US08946259B2

Reaction notes

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