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1,2-Dichloroethane → N-Ethylcarbamate 4,6-dichloro-5-methoxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

HRID 508524
Notes
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Reaction equation

HRID 508524 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][O:20][C:21]1C=C[C:24]2[CH:25]([CH3:33])[CH:26]3[CH2:30][NH:29][CH2:28][CH:27]3[C:31]=2[CH:32]=1.Cl[CH2:35][CH2:36][Cl:37]>>[CH2:13]([NH:15][C:16](=[O:17])[O-:18])[CH3:14].[Cl:37][C:36]1[C:35]2[CH:27]3[CH2:28][NH:29][CH2:30][CH:26]3[CH:25]([CH3:33])[C:24]=2[CH:31]=[C:32]([Cl:8])[C:21]=1[O:20][CH3:19]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 31398ChlorosuccinimideHCID 86602843N-Ethylcarbamate 5-methoxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Product 1

HCID 131728821N-Ethylcarbamate 4,6-dichloro-5-methoxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Conditions

Temperature
70 °C

Procedure

NCS (63 mg, 0.47 mmol) and acetic acid (1 mL) were added to a solution of N-ethylcarbamate-5-methoxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (from Example 2, Step A) (43 mg, 0.16 mmol) in DCE (1 mL), and the reaction solution was stirred for 3 hours at 70° C. The reaction was quenched with H2O and the solution filtered through an Extrelut column. The column was washed with CH2Cl2, and the filtrate was concentrated. The subtitle compound was obtained without further purification. MS calculated for C16H19Cl2NO3+H: 344, observed: 344.

Workup

  1. customThe reaction was quenched with H2O
  2. filtrationthe solution filtered through an Extrelut column
  3. washThe column was washed with CH2Cl2
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2edb7e02b81242878d1f5224e547b339
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09096520B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes