tert-Butanol → tert-Butyl (benzylsulfamoyl)carbamate

HRID 2189128Notes

Reaction equation

HRID 2189128 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[CH3:8][C:9]([OH:12])([CH3:11])[CH3:10].[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)Cl>[CH2:13]([NH:20][S:2]([NH:5][C:6]([O:12][C:9]([CH3:11])([CH3:10])[CH3:8])=[O:7])(=[O:4])=[O:3])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 7504BenzylamineHCID 70918Chlorosulfonyl isocyanate

Product 1

HCID 17757567tert-Butyl (benzylsulfamoyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

Chlorosulfonylisocyanate (14.14 g) was dissolved in DCM (50 mL) and cooled to 0° C. A solution of t-BuOH (9.6 mL) in DCM (50 mL) was added within 30 min. Stirring was continued for additional 30 min at rt. The solution thus obtained was then added at 0° C. within 1 h to a solution of benzylamine (10.7 g) and TEA (15.32 mL) in DCM (200 mL). Stirring is continued for 10 h at rt. The mixture was concentrated in vacuo, taken up in EA (500 mL) and washed with water (2×40 mL) and brine (30 mL), dried over MgSO4, filtered. The filtrate was concentrated in vacuo and the crude material was crystallized from EA and dried under HV to give N-benzyl-N′-tert-butoxycarbonyl sulfamide (13.68 g).

Workup

  1. customThe solution thus obtained
  2. stirringStirring
  3. waitis continued for 10 h at rt
  4. concentrationThe mixture was concentrated in vacuo
  5. washwashed with water (2×40 mL) and brine (30 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo
  9. customthe crude material was crystallized from EA
  10. customdried under HV

Sources & evidence

ORD record
ord-e131a55eb6d34e648fbb69dfcdf94b29
Source dataset
uspto-grants-2012_12
Patent number
US08324232B2

Reaction notes

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