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Hydrochloric Acid → HCID 67378569, compound

HRID 514772
Notes
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Reaction equation

HRID 514772 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.O.[Na].[N+:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25]([N:28]1[CH2:30][CH2:29]1)(=[O:27])=[O:26])([O-:18])=[O:17].Cl>CC#N.O.CCCCCC.C(OCC)(=O)C>[CH:10]1[C:11]2[N:12]([CH2:30][CH2:29][NH:28][S:25]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[N+:16]([O-:18])=[O:17])(=[O:26])=[O:27])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6854CarbazoleHCID 11183770HCID 11183770, compoundHCID 71353970Sodium monohydrate

Product 1

HCID 67378569HCID 67378569, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent
HCID 6342
Acetonitrile
Solvent
2×
HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Carbazole (1.10 g, 6.59 mmol) was dissolved in CH3CN (40 mL). Then sodium hydrate (0.33 g, 8.25 mmol) was added, and the mixture was stirred at room temperature for 15-20 min. Then, a solution of aziridine 56 (1.5 g, 7.89 mmol) in CH3CN (30 mL) was added in one portion. The resulting mixture was stirred for 1 h (TLC monitoring, eluent: hexane-ethyl acetate, 1:1), poured into water, acidified with HCl to pH 1, and stirred again at room temperature. Gradually, an orange product precipitated from the turbid solution. The precipitate was filtered, and washed with MeOH and ether. Yield of 51: 2.15 g (83%) as orange crystals.

Workup

  1. stirringstirred again at room temperature
  2. customGradually, an orange product precipitated from the turbid solution
  3. filtrationThe precipitate was filtered
  4. washwashed with MeOH and ether

Sources & evidence

ORD record
ord-ca038d7ebff349bea600394e95e01439
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09108916B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes