Triethylamine → HCID 67303576, compound

HRID 2061605Notes

Reaction equation

HRID 2061605 reaction equation
CS(Cl)(=O)=O.C(N(CC)CC)C.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([N:23]2[C:27]3[CH2:28][CH:29]4[N:34]([S:35]([C:38]5[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=5)(=[O:37])=[O:36])[CH:33]([C:26]=3[CH:25]=[N:24]2)[CH2:32][CH:31]([CH:45]=[N:46]O)[CH2:30]4)(=[O:22])=[O:21])=[CH:16][CH:15]=1.[Cl:48][C:49]1[CH:54]=[CH:53][C:52]([S:55]([N:58]2[CH2:62][C:61]3[CH:63]4[N:69]([S:70]([C:73]5[CH:78]=[CH:77][C:76]([Cl:79])=[CH:75][CH:74]=5)(=[O:72])=[O:71])[CH:67]([CH2:68][C:60]=3[NH:59]2)[CH2:66][CH:65]([CH:80]=[N:81]O)[CH2:64]4)(=[O:57])=[O:56])=[CH:51][CH:50]=1>C(Cl)Cl>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([S:20]([N:23]2[C:27]3[CH2:28][CH:29]4[N:34]([S:35]([C:38]5[CH:39]=[CH:40][C:41]([Cl:44])=[CH:42][CH:43]=5)(=[O:37])=[O:36])[CH:33]([C:26]=3[CH:25]=[N:24]2)[CH2:32][CH:31]([C:45]#[N:46])[CH2:30]4)(=[O:22])=[O:21])=[CH:18][CH:19]=1.[Cl:48][C:49]1[CH:50]=[CH:51][C:52]([S:55]([N:58]2[CH:62]=[C:61]3[CH:63]4[N:69]([S:70]([C:73]5[CH:74]=[CH:75][C:76]([Cl:79])=[CH:77][CH:78]=5)(=[O:72])=[O:71])[CH:67]([CH2:68][C:60]3=[N:59]2)[CH2:66][CH:65]([C:80]#[N:81])[CH2:64]4)(=[O:57])=[O:56])=[CH:53][CH:54]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 87350309HCID 87350309, compoundHCID 87350463HCID 87350463, compound

Product 2

HCID 67303576HCID 67303576, compoundHCID 67308401HCID 67308401, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methanesulfonyl chloride (30 μL, 0.390 mmol) and triethylamine (162 μL, 1.17 mmol) were added to a solution of 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) (73 mg, 0.130 mmol) in CH2Cl2 (1 mL) and the resulting solution was stirred at room temperature for 0.5 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 1,10-bis[(4-chlorophenyl)sulfonyl]-4,5,6,7,8,9-hexahydro-1H-4,8-epiminocycloocta[c]pyrazole-6-carbonitrile and 2,10-bis[(4-chlorophenyl)sulfonyl]-4,5,6,7,8,9-hexahydro-2H-4,8-epiminocycloocta[c]pyrazole-6-carbonitrile (61). MS (ESI) 537.0 (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-cc36f6685e3b4f5bb1183d50b0767a1f
Source dataset
uspto-grants-2012_10
Patent number
US08283358B2

Reaction notes

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