4-Toluenesulfonyl chloride → HCID 20510476, compound

HRID 1758019Notes

Reaction equation

HRID 1758019 reaction equation
[OH:1][N:2]([CH3:11])[C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.C1COCC1.C(N(CC)CC)C>C(Cl)Cl>[S:18]([O:1][N:2]([CH3:11])[C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([C:15]1[CH:16]=[CH:17][C:12]([CH3:22])=[CH:13][CH:14]=1)(=[O:20])=[O:19]

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 371715N-Hydroxy-N-methylbenzamide

Product 1

HCID 20510476HCID 20510476, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Tosyloxy-N-methylbenzamide was prepared by the following procedure. To a flask equipped with a stirrer were added N-hydroxy-N-methylbenzamide (1.39 g, 0.010 mol) from above, p-toluenesulfonyl chloride (1.91 g, 0.010 mol), 25 mL of THF and 2 mL of triethylamine. After 30 min at 0° followed by 1 h at room temperature, the reaction mixture was diluted with 50 mL of methylene chloride, and the solution was washed with water (4×50 mL) and dried. Evaporation of the solvent left 2.84 g of a golden oil which soon crystallized. Recrystallization from methylene chloride-hexane gave 2.04 g (69.4%) of fluffy white N-tosyloxy-N-methylbenzamide: mp 98°-99.5°; nmr (CDCl3) 7.8-7.0 (A2B2 and singlet at 7.36, 9H), 3.53 (s, 3H), 2.38 (s, 3H); ir (KBr) 1684 (vs), 1370 (s), 1180 (s), 1170 (s), 880 (m), 805 (m), 735 (m), 695 (s), 651 (m), 540 (s): uv (CH3CN) 227 (19,200), 265 (sh, 2020), 273 nm (sh, 1500); mass spectrum 305.0720 (calcd for C15H15O4NS: m+, 305.0720). Anal. Calcd for C15H15O4NS: C, 59.00; H, 4.95; N, 4.59; S, 20.96; O, 10.50. Found: C, 58.87, 58.75; H, 4.98, 5.02; N, 4.52, 4.43.

Workup

  1. customN-Tosyloxy-N-methylbenzamide was prepared by the following procedure
  2. customTo a flask equipped with a stirrer
  3. washthe solution was washed with water (4×50 mL)
  4. customdried
  5. customEvaporation of the solvent
  6. waitleft 2.84 g of a golden oil which
  7. customsoon crystallized
  8. customRecrystallization from methylene chloride-hexane

Sources & evidence

ORD record
ord-8980774a3775409596c7523bd30080b4
Source dataset
uspto-grants-1983_02
Patent number
US04371605

Reaction notes

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