Hydroxylamine → HCID 56932909, compound

HRID 1019667Notes

Reaction equation

HRID 1019667 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:18]=[C:19]([S:23](Cl)(=[O:25])=[O:24])[CH:20]=[CH:21][CH:22]=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:19]3[CH:20]=[CH:21][CH:22]=[C:17]([Cl:16])[CH:18]=3)(=[O:25])=[O:24])[CH2:8][C:7]=2[CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 14797Potassium HydroxideHCID 179093-Chlorobenzenesulphonyl chlorideHCID 58055425HCID 58055425, compound

Product 1

HCID 56932909HCID 56932909, 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 3-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 (m, 1H), 7.84 (d, 1H, J=8.0 Hz), 7.66 (d, 1H, J=8.4 Hz), 7.59 (t, 1H, J=8.0 Hz), 7.47 (d, 1H, J=8.0 Hz), 7.36 (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-1c0410f3e3ba42789df9fc9d0bad5dea
Source dataset
uspto-grants-2014_05
Patent number
US08716285B2

Reaction notes

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