Hydroxylamine → HCID 56932958, compound

HRID 1019671Notes

Reaction equation

HRID 1019671 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]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[S:24](Cl)(=[O:26])=[O:25].[OH:28][NH2:29].[OH-].[K+]>ClCCl>[OH:28][NH:29][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[CH2:11][CH2:10][CH:9]([NH:15][S:24]([C:18]3[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:17]=3[Cl:16])(=[O:26])=[O:25])[CH2:8][C:7]=2[CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 14797Potassium HydroxideHCID 204419Benzenesulfonyl chloride, 2,4-dichloro-HCID 58055425HCID 58055425, compound

Product 1

HCID 56932958HCID 56932958, 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 2,4-dichlorobenzenesulfonyl chloride and TEA in dichloromethane, and (2) treating the ester intermediate with aqueous HONH2 and KOH. MS: calc'd (MH+) 415, exp (MH+) 415.3. 1H NMR (CD3OD, 400 MHz), 8.09 (d, 1H, J=8.4 Hz), 7.70 (d, 1H, J=2.0 Hz), 7.54 (dd, 1H, J1=8.4 Hz, J2=2.0 Hz), 7.46 (d, 1H, J=8.0 Hz), 7.33 (s, 1H), 7.14 (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-6b215ba6f15f455cb139d920d96614f7
Source dataset
uspto-grants-2014_05
Patent number
US08716285B2

Reaction notes

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