Hydroxyamine hydrochloride → HCID 87350309, compound

HRID 2061604Notes

Reaction equation

HRID 2061604 reaction equation
Cl.[NH2:2][OH:3].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[C:18]3[CH2:19][CH:20]4[N:25]([S:26]([C:29]5[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=5)(=[O:28])=[O:27])[CH:24]([C:17]=3[CH:16]=[N:15]2)[CH2:23][CH:22]([CH:36]=O)[CH2:21]4)(=[O:13])=[O:12])=[CH:7][CH:6]=1.[Cl:38][C:39]1[CH:44]=[CH:43][C:42]([S:45]([N:48]2[CH:52]=[C:51]3[CH:53]4[N:59]([S:60]([C:63]5[CH:68]=[CH:67][C:66]([Cl:69])=[CH:65][CH:64]=5)(=[O:62])=[O:61])[CH:57]([CH2:58][C:50]3=[N:49]2)[CH2:56][CH:55]([CH:70]=O)[CH2:54]4)(=[O:47])=[O:46])=[CH:41][CH:40]=1>CCO.N1C=CC=CC=1.C(Cl)Cl>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[C:18]3[CH2:19][CH:20]4[N:25]([S:26]([C:29]5[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=5)(=[O:28])=[O:27])[CH:24]([C:17]=3[CH:16]=[N:15]2)[CH2:23][CH:22]([CH:36]=[N:2][OH:3])[CH2:21]4)(=[O:13])=[O:12])=[CH:7][CH:6]=1.[Cl:38][C:39]1[CH:44]=[CH:43][C:42]([S:45]([N:48]2[CH2:52][C:51]3[CH:53]4[N:59]([S:60]([C:63]5[CH:68]=[CH:67][C:66]([Cl:69])=[CH:65][CH:64]=5)(=[O:62])=[O:61])[CH:57]([CH2:58][C:50]=3[NH:49]2)[CH2:56][CH:55]([CH:70]=[N:2][OH:3])[CH2:54]4)(=[O:47])=[O:46])=[CH:41][CH:40]=1

Participants

7

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 87347838HCID 87347838, compoundHCID 87350243HCID 87350243, compound

Product 2

HCID 87350309HCID 87350309, compoundHCID 87350463HCID 87350463, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21975839Pyridine ethanolSolvent

Procedure

Hydroxylamine hydrochloride (18 mg, 0.252 mmol) was added to a solution of 1,10-bis[(4-chlorophenyl)sulfonyl]-4,5,6,7,8,9-hexahydro-1H-4,8-epiminocycloocta[c]pyrazole-6-carbaldehyde and 2,10-bis[(4-chlorophenyl)sulfonyl]-4,5,6,7,8,9-hexahydro-2H-4,8-epiminocycloocta[c]pyrazole-6-carbaldehyde (59) (91 mg, 0.168 mmol) in EtOH/pyridine (2 ml, 1/1, v/v) and the resulting solution was stirred at room temperature for 2 h. The reaction mixture was diluted with CH2Cl2 and washed with saturated aqueous NaHCO3. The organic phase was dried (Na2SO4), filtered and concentrated to give 1-{1,10-bis[(4-chlorophenyl)sulfonyl]-4,5,6,7,8,9-hexahydro-1H-4,8-epiminocycloocta[c]pyrazol-6-yl}-N-hydroxymethanimine and 1-{2,10-bis[(4-chlorophenyl)sulfonyl]-4,5,6,7,8,9-hexahydro-1H-4,8-epiminocycloocta[c]pyrazol-6-yl}-N-hydroxymethanimine (60). MS (ESI) 555.0 (M+H).

Workup

  1. washwashed with saturated aqueous NaHCO3
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8a537f78645342da8115f32fa2b8816c
Source dataset
uspto-grants-2012_10
Patent number
US08283358B2

Reaction notes

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