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Acetic Acid → N-Ethylcarbamate 5-methyl-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

HRID 1517698
Notes
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Reaction equation

HRID 1517698 reaction equation
C1C(=O)N([Cl:8])C(=O)C1.C(O)(=O)C.[CH2:13]([NH:15][C:16](=[O:18])[O-:17])[CH3:14].[CH3:19][C:20]1[CH:21]=[CH:22][C:23]2[CH:24]([CH3:32])[CH:25]3[CH2:29][NH:28][CH2:27][CH:26]3[C:30]=2[CH:31]=1>ClCCCl.C(Cl)Cl.O>[CH2:13]([NH:15][C:16](=[O:17])[O-:18])[CH3:14].[CH3:19][C:20]1[C:21]([Cl:8])=[CH:22][C:23]2[CH:24]([CH3:32])[CH:25]3[CH2:29][NH:28][CH2:27][CH:26]3[C:30]=2[CH:31]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 31398ChlorosuccinimideHCID 86602856HCID 86602856, compound

Product 1

HCID 86602857N-Ethylcarbamate 5-methyl-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolvent
HCID 962
Water
Solvent
HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

NCS (27 mg, 0.2 mmol) and acetic acid (1 mL) were added to a solution of N-Ethylcarbamate-5-methyl-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (50 mg, 0.2 mmol) in DCE (1 mL). The reaction solution was stirred for 3 hours at 60° C. The reaction was diluted with CH2Cl2 (3 mL) and H2O (3 mL) and filtered through an Extrelut column. The column was washed with CH2Cl2 and the filtrate was concentrated. The crude product was purified by column chromatography (SiO2) using a 0-60% ethyl acetate-hexanes gradient to afford the subtitle compound. MS calculated for C16H20ClNO2+H: 294, observed: 294.

Workup

  1. filtrationfiltered through an Extrelut column
  2. washThe column was washed with CH2Cl2
  3. concentrationthe filtrate was concentrated
  4. customThe crude product was purified by column chromatography (SiO2)

Sources & evidence

ORD record
ord-30cf377b941243f488c74ddd47aae999
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08232311B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes