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Hydrochloric Acid → 2-{2[2-(5-Bromo-2-methoxy-phenyl)-ethyl]-3-chloro-phenyl}-3a,4,5,6,7,7a-hexahydro-1H-benzoimidazole

HRID 2223328
Notes
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Reaction equation

HRID 2223328 reaction equation
C(S[C:4](=S)[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:6]=1[CH2:12][CH2:13][C:14]1[CH:19]=[C:18]([Br:20])[CH:17]=[CH:16][C:15]=1[O:21][CH3:22])C.Cl.[NH2:25][C@@H:26]1[CH2:31][CH2:30][CH2:29][CH2:28][C@H:27]1[NH2:32]>O>[Br:20][C:18]1[CH:17]=[CH:16][C:15]([O:21][CH3:22])=[C:14]([CH2:13][CH2:12][C:6]2[C:7]([Cl:11])=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]2[NH:32][CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31][CH:26]3[N:25]=2)[CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 438061,2-Diaminocyclohexane, trans-HCID 206283942-[2-(5-Bromo-2-methoxy-phenyl)-ethyl]-3-chloro-dithiobenzoic acid ethyl ester

Product 1

HCID 227447592-{2[2-(5-Bromo-2-methoxy-phenyl)-ethyl]-3-chloro-phenyl}-3a,4,5,6,7,7a-hexahydro-1H-benzoimidazole

Reagents, catalysts & solvents 1

HCID 962Water
Solvent

Procedure

As shown in Scheme 25, a solution of 187 mg (0.43 mmol) of 2-[2-(5-Bromo-2-methoxy-phenyl)-ethyl]-3-chloro-dithiobenzoic acid ethyl ester in 2.5 mL of trans-1,2 diaminocyclohexane was heated to 110° C. in a sealed pressure tube for 12 hours. The reaction mixture was diluted with water and extracted with methylene chloride twice. The organic extracts were washed with brine, dried (MgSO4) and evaporated. The residue was chromatographed on silica gel (eluting with 95:5 CH2Cl2/methanol) to give a yellow oil. The oil was treated with methanolic HCl and evaporated to yield 34 mg of product as a pure hydrochloride salt.

Workup

  1. extractionextracted with methylene chloride twice
  2. washThe organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was chromatographed on silica gel (eluting with 95:5 CH2Cl2/methanol)
  6. customto give a yellow oil
  7. customevaporated

Sources & evidence

ORD record
ord-89a4d5485ca1436e9fdc33c04302b082
Source dataset
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07375125B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes