Dichloromethane → HCID 59822278, compound

HRID 1670553Notes

Reaction equation

HRID 1670553 reaction equation
Cl.[Cl:2][C:3]1[CH:13]=[CH:12][C:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11][C:5]=2[C:4]=1[CH2:14][S:15][C:16]1[NH:17][CH:18]=[CH:19][N:20]=1.C([O-])([O-])=O.[Na+].[Na+].C(Cl)Cl>O.C(O)C>[Cl:2][C:3]1[CH:13]=[CH:12][C:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11][C:5]=2[C:4]=1[CH2:14][S:15][C:16]1[NH:20][CH:19]=[CH:18][N:17]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 67336483HCID 67336483, compound

Product 1

HCID 59822278HCID 59822278, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Dissolve 7-chloro-6-(1H-imidazol-2-ylthiomethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochloride (9.85 g, 29.85 mmol) in water (60 mL) and absolute ethanol (40 mL) in a flask. Add a solution of Na2CO3 (15.8 g, 149 mmol) in water (100 mL) followed by DCM (125 mL) to the flask. Stir the mixture vigorously, then separate layers. Extract the aqueous layer twice with a solution of DCM (100 mL) and ethanol (10 mL). Dry the combined organic extracts over Na2SO4. Filter and concentrate in vacuo to obtain 7-chloro-6-(1H-imidazol-2-ylthiomethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a light yellow foam (7.4 g, 75% weight recovery). MS (APCI+) m/z: 294.25 (M+H)+.

Workup

  1. extractionExtract the aqueous layer twice with a solution of DCM (100 mL) and ethanol (10 mL)
  2. dry with materialDry the combined organic extracts over Na2SO4
  3. filtrationFilter
  4. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-cf21b55e063a4577b20af9d8cf6b3744
Source dataset
uspto-grants-2011_08
Patent number
US07994163B2

Reaction notes

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