Hydroxylamine → HCID 56932908, compound

HRID 1019666Notes

Reaction equation

HRID 1019666 reaction equation
CO[C:3]([C:5]1[CH:14]=[CH:13][C:12]2[CH2:11][CH2:10][CH:9]([NH2:15])[CH2:8][C:7]=2[CH:6]=1)=[O:4].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.[OH:27][NH2:28].[OH-].[K+]>ClCCl>[OH:27][NH:28][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[CH2:11][CH2:10][CH:9]([NH:15][S:23]([C:20]3[CH:21]=[CH:22][C:17]([Cl:16])=[CH:18][CH:19]=3)(=[O:25])=[O:24])[CH2:8][C:7]=2[CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 73984-Chlorobenzenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 58055425HCID 58055425, compound

Product 1

HCID 56932908HCID 56932908, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared in two steps according to Scheme 6 by (1) treating amine VII with 4-chlorobenzenesulfonyl chloride and TEA in dichloromethane, and (2) treating the ester intermediate with aqueous HONH2 and KOH. MS: calc'd (MH+) 381, exp (MH+) 381. 1H NMR (CD3OD, 400 MHz), 7.90 (d, 2H, J=8.4 Hz), 7.60 (d, 2H, J=8.4 Hz), 7.47 (d, 1H, J=8.0 Hz), 7.37 (s, 1H), 7.15 (d, 1H, J=8.0 Hz), 3.55 (m, 1H), 2.95 (m, 2H), 2.82 (m, 1H), 2.69 (m, 1H), 1.95 (m, 1H) 1.73 (m, 1H).

Sources & evidence

ORD record
ord-51c714a94c1f42bfb99c8647232732b2
Source dataset
uspto-grants-2014_05
Patent number
US08716285B2

Reaction notes

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