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

HRID 1192885ノート

反応式

HRID 1192885 の反応式
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]

参加物

7

反応物 5

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

生成物 1

HCID 581099762-chloroethyl N-(4-octylphenyl)sulfamoylcarbamate収率 40.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6226fd46749140e7b60ad24aa7212bce
出典データセット
uspto-grants-2014_03
特許番号
US08680282B2

反応ノート

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