Water → Tert-butyl 1-(4-(3-phenylureido)phenylsulfonyl)-1,2,3,4-tetrahydroquinolin-3-ylcarbamate

HRID 2389558Notes

Reaction equation

HRID 2389558 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH:13]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH2:29]>ClCCCl>[C:20]1([NH:11][C:12](=[O:29])[NH:1][C:2]2[CH:3]=[CH:4][C:5]([S:8]([N:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH2:14][CH:13]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:27])[CH3:26])[CH2:12]3)(=[O:10])=[O:9])=[CH:6][CH:7]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 962WaterHCID 59400239Tert-butyl 1-(4-aminophenylsulfonyl)1,2,3,4-tetrahydroquinolin-3-ylcarbamate

Product 1

HCID 59400148Tert-butyl 1-(4-(3-phenylureido)phenylsulfonyl)-1,2,3,4-tetrahydroquinolin-3-ylcarbamate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

tert-butyl 1-(4-aminophenylsulfonyl)-1,2,3,4-tetrahydroquinolin-3-ylcarbamate (60.5 mg, 0.15 mmol) and isocyantobenzene (17.8 mg, 0.15 mmol) in 1,2-dichloroethane (3 mL) were stirred at room temperature for 20 hours. Water (1.5 mL) was added and the mixture extracted with ethyl acetate (3×1.5 mL). The combined organics were dried over sodium sulfate and concentrated to give tert-butyl 1-(4-(3-phenylureido)phenylsulfonyl)-1,2,3,4-tetrahydroquinolin-3-ylcarbamate.

Workup

  1. extractionthe mixture extracted with ethyl acetate (3×1.5 mL)
  2. dry with materialThe combined organics were dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-46e74c914f8a43c5afacc01998c38fb7
Source dataset
uspto-grants-2012_09
Patent number
US08273754B2

Reaction notes

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