4-Toluenesulfonyl chloride → HCID 20510480, compound

HRID 1758016Notes

Reaction equation

HRID 1758016 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[C:8]([Cl:15])[C:9]([Cl:14])=[C:10]([Cl:13])[C:11]([Cl:12])=[C:4]2[C:3]1=[O:16].[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.C(N(CC)CC)C>O1CCCC1.C(Cl)Cl>[S:23]([O:1][N:2]1[C:3](=[O:16])[C:4]2=[C:11]([Cl:12])[C:10]([Cl:13])=[C:9]([Cl:14])[C:8]([Cl:15])=[C:5]2[C:6]1=[O:7])([C:20]1[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=1)(=[O:25])=[O:24]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 287359N-hydroxytetrachlorophthalimide

Product 1

HCID 20510480HCID 20510480, compoundYield 89.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

N-Tosyloxytetrachlorophthalimide was prepared by the following procedure. To a flask equipped with a stirrer and addition funnel were added N-hydroxytetrachlorophthalimide (10.00 g, 0.033 mol), p-toluenesulfonyl chlorde (6.57 g, 0.033 mol) and 100 mL of dried tetrahydrofuran (THF). A solution of triethylamine (4.5 mL, 0.033 mol) in 20 mL of THF was added dropwise while the reaction vessel was cooled to between -20° and -10°. A red color formed after each drop, and quickly disappeared. After stirring for 2 h at room temperature the reaction mixture was diluted with 200 mL of methylene chloride, and the solution was washed twice with water. The organic layer containing much crystallized product was evaporated, leaving 13.5 g of pale yellow N-tosyloxytetrachlorophthalimide: mp 206°-210°. Recrystallization from toluene (50 mL)-heptane (25 mL) gave 10.7 g (71.5%) of pale yellow product: mp 214°-216°; ir (KBr) 1800 (w), 1740 (vs), 1380 (m), 1190 (m), 1180 (m), 1140 (m), 1025 (m), 810 (m), 790 (m), 725 (m), 705 (m), 506 (m); uv (CH3CN) 240 (58,500), 275 (2990), 328 (2790), 339 nm (3020); mass spectrum 452.8782 (calcd for C15H7NO5Cl4S: m+, 452.8805). Anal. Calcd for C15H7NO5Cl4S: C, 39.59; H, 1.55; N, 3.08; O, 17.58; Cl, 31.16; S, 70.4. Found: C, 40.04, 40.16, 39.70, 39.72; H, 1.95, 1.81, 1.52, 1.70; N, 2.99, 2.89; Cl, 31.30.

Workup

  1. customN-Tosyloxytetrachlorophthalimide was prepared by the following procedure
  2. customTo a flask equipped with a stirrer and addition funnel
  3. temperaturewas cooled to between -20° and -10°
  4. customA red color formed after each drop
  5. washthe solution was washed twice with water
  6. additionThe organic layer containing much crystallized product
  7. customwas evaporated

Sources & evidence

ORD record
ord-0a52d0e5cd6445978fd970ff36e1c098
Source dataset
uspto-grants-1983_02
Patent number
US04371605

Reaction notes

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