Triethylamine → [1,1':3', 1"-Terphenyl]-2'-yl[[[2,6-bis(1-methylethyl)phenyl]amino]sulfonyl]carbamat

HRID 1742033Notes

Reaction equation

HRID 1742033 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:8]=2[O:19][C:20](=[O:26])[NH:21][S:22](Cl)(=[O:24])=[O:23])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:27]([C:30]1[CH:36]=[CH:35][CH:34]=[C:33]([CH:37]([CH3:39])[CH3:38])[C:31]=1[NH2:32])([CH3:29])[CH3:28].C(N(CC)CC)C>O1CCCC1>[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:8]=2[O:19][C:20](=[O:26])[NH:21][S:22]([NH:32][C:31]2[C:33]([CH:37]([CH3:38])[CH3:39])=[CH:34][CH:35]=[CH:36][C:30]=2[CH:27]([CH3:29])[CH3:28])(=[O:24])=[O:23])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 32484DiisopropylanilineHCID 10572313[1,1':3',1"-Terphenyl]-2'-yl(chlorosulfonyl)carbamate

Product 1

HCID 10506346[1,1':3', 1"-Terphenyl]-2'-yl[[[2,6-bis(1-methylethyl)phenyl]amino]sulfonyl]carbamat

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of [1,1':3', 1"-terphenyl]-2'-yl(chlorosulfonyl)carbamate (5.0 g, 12.9 mmol) in 75 mL tetrahydrofuran was added dropwise to a solution of 2,6-diisopropyl aniline (2.29 g, 12.9 mmol) and triethylamine (1.3 g, 12.9 mmol) in 100 mL tetrahydrofuran at -15° C. under an atmosphere of nitrogen. The resulting mixture was warmed to room temperature and stirred for 16 hours. Concentrated in vacuo and partitioned the residue between water and ethyl acetate. Dried the organic layer over MgSO4 and evaporated to give an off-white solid. Chromatography on silica gel gave the title compound, mp 166°-168° C.

Workup

  1. concentrationConcentrated in vacuo
  2. custompartitioned the residue between water and ethyl acetate
  3. dry with materialDried the organic layer over MgSO4
  4. customevaporated
  5. customto give an off-white solid

Sources & evidence

ORD record
ord-f09b8a53804a4aa4abd7076939c4f1b7
Source dataset
uspto-grants-1994_08
Patent number
US05336690

Reaction notes

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