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Triethylamine → toluene-4-thiosulfonic acid S-(2-tert-butyl-4-ethylsulfamoyloxy-5-methyl-phenyl) ester

HRID 356511
Notes
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Reaction equation

HRID 356511 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([OH:11])[C:8]([CH3:12])=[CH:7][C:6]=1[S:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)(=[O:16])=[O:15])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH2:31]([NH:33][S:34](Cl)(=[O:36])=[O:35])[CH3:32]>CCOCC>[C:1]([C:5]1[CH:10]=[C:9]([O:11][S:34](=[O:36])(=[O:35])[NH:33][CH2:31][CH3:32])[C:8]([CH3:12])=[CH:7][C:6]=1[S:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)(=[O:15])=[O:16])([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10521842Toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxy-5-methyl-phenyl) esterHCID 11040810Ethylsulfamoyl chloride

Product 1

HCID 10551814toluene-4-thiosulfonic acid S-(2-tert-butyl-4-ethylsulfamoyloxy-5-methyl-phenyl) ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl Ether
Solvent
2×

Conditions

Temperature
0 °C

Procedure

To a round bottom flask equipped with a magnetic stirrer and nitrogen were added toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxy-5-methyl-phenyl) ester (prepared in Example RRR; 6.86 g, 19.6 mmol), Et2O (100 mL), and NEt3 (3.25 mL, 23.4 mmol), respectively. The solution was cooled to 0° C. and treated rapidly with a solution of (ethyl amino)sulfonyl chloride (3.37 g, 23.4 mmol) in Et2O (10 mL). The reaction was stirred for 30 minutes and then filtered. The solids were washed with Et2O, and the filtrate was concentrated. The resulting residue was dried in a high vacuum oven at 40° C. overnight to yield the title compound. 1H NMR (CDCl3) δ 1.15 (s, 9 H), 1.23 (t, 3 H) 2.19 (s, 3 H), 2.35 (s, 3 H), 3.30 (m, 2 H), 4.75 (br t, 1 H), 7.16 (s, 1 H), 7.19 (s, 1 H), 7.32 (d, 2 H), 7.39 (d, 2 H).

Workup

  1. customTo a round bottom flask equipped with a magnetic stirrer
  2. filtrationfiltered
  3. washThe solids were washed with Et2O
  4. concentrationthe filtrate was concentrated
  5. customThe resulting residue was dried in a high vacuum oven at 40° C. overnight

Sources & evidence

ORD record
ord-0b84994149df4053b38e927c5e1551fa
Source dataset
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05834506

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes