Water → Ethyl 1-(3,4-dichlorobenzyl)-7-(2-(1-methyl-1H-imidazole-4-sulfonamido)ethoxy)-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate

HRID 2177066Notes

Reaction equation

HRID 2177066 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][CH:12]([NH:25][C:26](=[O:30])[O:27][CH2:28][CH3:29])[CH:13]2[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)=[CH:8][CH:7]=1.[CH3:31][N:32]1[CH:36]=[C:35]([S:37](Cl)(=[O:39])=[O:38])[N:34]=[CH:33]1.O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:24][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][C:20]=1[Cl:23])[CH2:16][CH:13]1[C:14]2[C:9](=[CH:8][CH:7]=[C:6]([O:5][CH2:4][CH2:3][NH:2][S:37]([C:35]3[N:34]=[CH:33][N:32]([CH3:31])[CH:36]=3)(=[O:39])=[O:38])[CH:15]=2)[CH2:10][CH2:11][CH:12]1[NH:25][C:26](=[O:30])[O:27][CH2:28][CH3:29]

Participants

6

Reactant 3

HCID 962WaterHCID 27368871-methyl-1H-imidazole-4-sulfonyl chlorideHCID 68516136Ethyl 7-(2-aminoethoxy)-1-(3,4-dichlorobenzyl)-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate hydrochloride

Product 1

HCID 46870449Ethyl 1-(3,4-dichlorobenzyl)-7-(2-(1-methyl-1H-imidazole-4-sulfonamido)ethoxy)-1,2,3,4-tetrahydronaphthalen-2-ylcarbamateYield 75.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Ethyl 7-(2-aminoethoxy)-1-(3,4-dichlorobenzyl)-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate hydrochloride (100 mg, 0.229 mmol) and DMAP (27.9 mg, 0.229 mmol) were dissolved in CH2Cl2 (15 ml) and 1-methyl-1H-imidazole-4-sulfonyl chloride (41.3 mg, 0.229 mmol) dissolved in CH2Cl2 (15 ml) was added. The reaction mixture was stirred over night at RT. After addition of H2O the phases were separated and the aqueous phase was extracted with CH2Cl2. The organic layer was washed with HCl (1N), NaHCO3 solution and NaCl solution, then dried on MgSO4 and the solvent was removed. To the residue EtOAc/diethylether (1:1) was added, stirred, and the precipitate was separated by filtration to obtain a brown solid of product (100 mg).

Workup

  1. additionwas added
  2. customwere separated
  3. extractionthe aqueous phase was extracted with CH2Cl2
  4. washThe organic layer was washed with HCl (1N), NaHCO3 solution and NaCl solution
  5. customdried on MgSO4
  6. customthe solvent was removed
  7. additionTo the residue EtOAc/diethylether (1:1) was added
  8. stirringstirred
  9. customthe precipitate was separated by filtration

Sources & evidence

ORD record
ord-d2b5131b5bed4629b76ba3350d488afa
Source dataset
uspto-grants-2015_06
Patent number
US09067871B2

Reaction notes

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