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

HRID 2201686Notes

Reaction equation

HRID 2201686 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-558b8f74bc734a698f5071961685636d
Source dataset
uspto-grants-2016_06
Patent number
US09365498B2

Reaction notes

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