4'-Methanesulphonyl-2-nitrobiphenyl → 4'-(Methylsulfonyl)[1,1'-biphenyl]-2-amine

HRID 1464047Notes

Reaction equation

HRID 1464047 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-])=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3]>C(O)C>[NH2:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:8]1[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 190892734'-Methanesulphonyl-2-nitrobiphenyl

Product 1

HCID 190892714'-(Methylsulfonyl)[1,1'-biphenyl]-2-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-methanesulphonyliodobenzene (18 g), 2-bromonitrobenzene (12.7 g) and copper powder (12 g) was heated at 120° C. for 30 hours to yield a residue which was purified by chromatography on a silica column eluted successively with 5:95 mixture, a 10:90 mixture, a 25:75 mixture and then a 40:60 mixture of ethylacetate and hexane to give 4'-methanesulphonyl-2-nitrobiphenyl (m.p. 178° C.). 4'-methanesulphonyl-2-nitrobiphenyl (5 g) was heated at 90°-95° C. for 6 hours with hydrated sodium sulphide (17.3 g) and ethanol (100 ml) to give 2-amino-4'-methanesulphonylbiphenyl (m.p. 164°-165° C.).

Sources & evidence

ORD record
ord-4e2f02225d1b40ca81c55bbf58794db4
Source dataset
uspto-grants-1994_04
Patent number
US05302720

Reaction notes

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