Hydrochloric Acid → Ethyl (2-amino-5-(thiophen-2-yl)phenyl)carbamate

HRID 62679

Reaction equation

HRID 62679 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([NH:12]C(=O)OC(C)(C)C)=[C:8]([NH:20][C:21](=[O:25])[O:22][CH2:23][CH3:24])[CH:7]=1.Cl>CO.O1CCOCC1>[NH2:12][C:9]1[CH:10]=[CH:11][C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[CH:7][C:8]=1[NH:20][C:21](=[O:25])[O:22][CH2:23][CH3:24]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 71007309Tert-butyl ethyl (4-(thiophen-2-yl)-1,2-phenylene)dicarbamate

Product 1

HCID 86712524Ethyl (2-amino-5-(thiophen-2-yl)phenyl)carbamateYield 69%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of tert-butyl ethyl (4-(thiophen-2-yl)-1,2-phenylene)dicarbamate (0.10 g, 0.28 mmol, 1.0 equiv.) in MeOH (2 mL) at 0° C. was added a 4M solution of HCl in dioxane (1.5 mL). The reaction was warmed to room temperature and stirred for 2 h, The reaction was concentrated under reduced pressure. A saturated aqueous solution of sodium bicarbonate was added. The obtained solid was filtered, washed with water and dried. The crude material was purified by column chromatography (silica gel, 15% EtOAc/hexanes) to give ethyl (2-amino-5-(thiophen-2-yl)phenyl)carbamate (0.05 g, 69% yield).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. additionA saturated aqueous solution of sodium bicarbonate was added
  3. filtrationThe obtained solid was filtered
  4. washwashed with water
  5. customdried
  6. customThe crude material was purified by column chromatography (silica gel, 15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7e13d12884744bc8a59977d3e9b152f1
Source dataset
uspto-grants-2016_09
Patent number
US09447030B2

Linked notes

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