Aniline → HCID 131732175, compound

HRID 1403725Notes

Reaction equation

HRID 1403725 reaction equation
[S:1](Cl)([N:4]=[C:5]=[O:6])(=[O:3])=[O:2].C[C:9]([OH:12])([CH3:11])C.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH2:20](N(CC)CC)[CH3:21]>C(Cl)Cl>[C:14]1([NH:13][S:1]([NH:4][C:5](=[O:6])[O:12][CH2:9][CH2:11][CH2:20][CH3:21])(=[O:3])=[O:2])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 6386tert-ButanolHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanate

Product 1

HCID 131732175HCID 131732175, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sulfurisocyanatidic chloride (5.5 g, 39.05 mmol) was dropped into a solution of t-BuOH (2.89 g, 39.05 mmol) in DCM (100 mL) at 0° C., followed by addition of aniline (7.3 g, 78.10 mmol) and triethylamine (7.9 g, 78.10 mmol). The mixture was stirred at ambient temperature for 2 hours. The mixture was washed with water. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to afford tent-butyl N-phenylsulfamoylcarbamate as white solid (9.5 g, 90%). LCMS (ESI): m/z=272.9 [M+H]+.

Workup

  1. washThe mixture was washed with water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-71534c84cc8d41eda517db99421ad362
Source dataset
uspto-grants-2014_12
Patent number
US08912219B2

Reaction notes

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