1-Dodecanol → [1,1':3',1"-Terphenyl]-2'-yl[(dodecyloxy)sulfonyl]carbamate

HRID 1769987Notes

Reaction equation

HRID 1769987 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.[CH2:27]([OH:39])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38].C(N(CC)CC)C>C1COCC1>[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]([O:39][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])(=[O:24])=[O:23])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 81931-DodecanolHCID 8471TriethylamineHCID 10572313[1,1':3',1"-Terphenyl]-2'-yl(chlorosulfonyl)carbamate

Product 1

HCID 15233160[1,1':3',1"-Terphenyl]-2'-yl[(dodecyloxy)sulfonyl]carbamateYield 42.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of [1,1':3',1"-terphenyl]-2'-yl(chlorosulfonyl)carbamate (5.0 g, 12.9 moles) in 75 mL THF was added dropwise to a solution of n-dodecyl alcohol (2.4 g, 12.9 mmoles) and triethylamine (1.3 g, 12.9 mmoles) in 100 mL THF at ~15° C. under an atmosphere of N2. The mixture was allowed to warm to room temperature for 16 hours, then concentrated in vacuo and partitioned between H2O and EtOAc. The EtOAc layer was dried with MgSO4 and evaporated to give a white solid. Chromatography (SiO2, 10% EtOAc/hexanes) gave 2.95 g of the title compound, mp 124°-126° C.

Workup

  1. concentrationconcentrated in vacuo
  2. custompartitioned between H2O and EtOAc
  3. dry with materialThe EtOAc layer was dried with MgSO4
  4. customevaporated
  5. customto give a white solid

Sources & evidence

ORD record
ord-f7fa307478ee40b5a59eb0831297e39c
Source dataset
uspto-grants-1995_01
Patent number
US05384328

Reaction notes

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