Dimethylamine → 3-amino-N,N-dimethylbenzene-1-sulfonamide

HRID 964636

Reaction equation

HRID 964636 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10](Cl)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[NH:14]([CH3:16])[CH3:15].CCN(C(C)C)C(C)C.Cl[Sn]Cl>C(Cl)Cl.CCOC(C)=O>[CH3:15][N:14]([CH3:16])[S:10]([C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[NH2:1])(=[O:12])=[O:11]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 84763-Nitrobenzenesulfonyl chlorideHCID 24479Stannous ChlorideHCID 81531Diisopropylethylamine

Product 1

HCID 2355203-amino-N,N-dimethylbenzene-1-sulfonamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following the procedure described in part E of Example 1 (R), (S)-α-[[2-[((1,1-dimethylethyl)dimethylsilyl)oxy]-2-[4-hydroxy-3-[(methylsulfonyl)amino]phenyl]ethyl]amino]-4-methoxybenzeneacetic acid was condensed with 3-[(dimethylamino)sulfonyl]aniline to generate the title compound. The 3-[(dimethylamino)sulfonyl]aniline was prepared by sequential treatment of commercial 3-nitrobenzenesulfonyl chloride with Me2NH in CH2Cl2 containing (i-Pr)2NEt followed by reduction with SnCl2 in EtOAc at 20° C.

Sources & evidence

ORD record
ord-927dc624ac08435ba16a97ce88a8e884
Source dataset
uspto-grants-1998_06
Patent number
US05770615

Linked notes

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