Triethylamine → HCID 56648956, compound

HRID 244506Notes

Reaction equation

HRID 244506 reaction equation
[C:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCN(CC)CC.[C:23]1([S:33](Cl)(=[O:35])=[O:34])[C:24]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:26]=[CH:27][CH:28]=1>C(Cl)Cl>[O:34]=[S:33]1(=[O:35])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[S:29](=[O:30])(=[O:31])[N:15]1[C:12]1[CH:11]=[CH:10][C:9]([NH:8][C:1](=[O:2])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 246432Benzene-1,2-disulfonyl dichlorideHCID 688611tert-Butyl (4-aminophenyl)carbamate

Product 1

HCID 56648956HCID 56648956, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of N-Boc-p-phenylenediamine (0.68 g, 3.26 mmol) and Et3N (0.51 mL, 7.19 mmol) in dry DCM (29 mL) was added to a refluxing solution of 1,2-benzenedisulfonyl dichloride (0.90 g, 3.27 mmol) in DCM (135 mL). After the addition was complete, the reaction solution was maintained at reflux for an additional 2 h. The heat was removed and after 16 h at rt, the solvent was removed under reduced pressure. The residue of the crude reaction mixture was dissolved in DCM and washed with saturated NaHCO3, brine, and dried. After filtration and concentration under reduced pressure yielding tert-butyl (4-(1,1,3,3-tetraoxidobenzo[d][1,3,2]dithiazol-2-yl)phenyl)carbamate, 1.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction solution was maintained
  3. temperatureat reflux for an additional 2 h
  4. customThe heat was removed and after 16 h at rt
  5. customthe solvent was removed under reduced pressure
  6. customThe residue of the crude reaction mixture
  7. washwashed with saturated NaHCO3, brine
  8. customdried
  9. filtrationAfter filtration and concentration under reduced pressure

Sources & evidence

ORD record
ord-19343db490584ac79a6c53e895365b7e
Source dataset
uspto-grants-2014_02
Patent number
US08658650B2

Reaction notes

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