2-Chloroethanol → 2-chloroethyl N-(4-octylphenyl)sulfamoylcarbamate

HRID 1192885Notes

Reaction equation

HRID 1192885 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[Cl:8][CH2:9][CH2:10][OH:11].[CH2:12]([C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C(N(CC)CC)C.S(Cl)(=O)(=O)N>ClCCl>[CH2:12]([C:20]1[CH:21]=[CH:22][C:23]([NH:24][S:2]([NH:5][C:6](=[O:7])[O:11][CH2:10][CH2:9][Cl:8])(=[O:4])=[O:3])=[CH:25][CH:26]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 5

HCID 342-ChloroethanolHCID 8471TriethylamineHCID 24499Chlorosulfamic acidHCID 70918Chlorosulfonyl isocyanateHCID 853464-Octylaniline

Product 1

HCID 581099762-chloroethyl N-(4-octylphenyl)sulfamoylcarbamateYield 40.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of chlorosulfonyl isocyanate (1.41 g, 10 mmol) in dichloromethane (5 mL) was treated with 2-chloroethanol (810 mg, 10 mmol) and stirred for 10 min at rt. The resulting solution was stored at ˜5° C.; aliquots were used as required. For example a solution of 4-n-octylaniline (2.05 g, 10 mmol) and triethylamine (1.54 mL, 11 mmol) in dichloromethane (20 mL) at 0° C. was treated dropwise with the solution of sulfamoyl chloride prepared as described above. After the addition was complete, the resulting mixture was stirred for 60 min at 0° C. and diluted with dichloromethane (40 mL). The dichloromethane solution was washed with 0.1 N HCl (20 mL), dried (Na2SO4) and concentrated to reduce the volume. The resultant white precipitate was collected by suction filtration to give the title compound (1.60 g) as white solid. Further concentration of the filtrate yielded an additional batch (1.02 g) as white solid. Total yield was 2.62 g (67%). 1H NMR (400 MHz, CDCl3) δ 7.21 (s, 1H), 7.20-7.10 (m, 4H), 7.11 (s, 1H), 4.46 (s, 2H), 3.71 (s, 2H), 2.60 (t, 2H, J=6.8 Hz), 1.58 (s, 2H), 1.37-1.20 (m, 10H), 0.88 (t, 3H, J=6.4 Hz).

Workup

  1. customwas stored at ˜5° C.
  2. customat 0° C.
  3. customprepared
  4. additionAfter the addition
  5. stirringthe resulting mixture was stirred for 60 min at 0° C.
  6. washThe dichloromethane solution was washed with 0.1 N HCl (20 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. filtrationThe resultant white precipitate was collected by suction filtration

Sources & evidence

ORD record
ord-6226fd46749140e7b60ad24aa7212bce
Source dataset
uspto-grants-2014_03
Patent number
US08680282B2

Reaction notes

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