Triethylamine → HCID 18983344, compound

HRID 1729500Notes

Reaction equation

HRID 1729500 reaction equation
CS(Cl)(=O)=O.[N+:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][OH:16])([O-:8])=[O:7].C(N([CH2:22][CH3:23])CC)C.[O:24]1[CH2:29][CH2:28]OCC1>>[CH3:15][C:10]1[CH:9]=[CH:22][C:23]([O:16][CH2:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N+:6]([O-:8])=[O:7])=[C:28]([CH:11]=1)[CH:29]=[O:24]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 119232-Nitrobenzyl alcoholHCID 312751,4-DioxaneHCID 31297Methanesulfonyl chloride

Product 1

HCID 18983344HCID 18983344, compound

Conditions

Temperature
20 °C

Procedure

Methanesulphonyl chloride (5.4 ml) was added dropwise to a stirred solution of 2-nitrobenzenemethanol (10.0 g) and triethylamine (10.1 ml) in 1,4-dioxane (10 ml) at 15°-25° C. After 30 min the mixture was filtered, washed with 1,4-dioxane (50 ml) and the filtrate added to a stirred mixture of 5-methylsalicylaldehyde (9.1 g) and potassium carbonate (9.9 g) in N,N-dimethylacetamide (50 ml). The mixture was stirred at 20° C. for 24 h, water (160 ml) was added and, after a further 1 h, the mixture was filtered. The filtrate was washed with water:1,4-dioxane (1:1; 50 ml) and water (150 ml) and dried at 40° C. in vacuo to give the title compound as a cream coloured solid (15.7 g) m.p. 124° C.

Workup

  1. filtrationAfter 30 min the mixture was filtered
  2. washwashed with 1,4-dioxane (50 ml)
  3. additionthe filtrate added to a stirred mixture of 5-methylsalicylaldehyde (9.1 g) and potassium carbonate (9.9 g) in N,N-dimethylacetamide (50 ml)
  4. additionwater (160 ml) was added and, after a further 1 h
  5. filtrationthe mixture was filtered
  6. washThe filtrate was washed with water:1,4-dioxane (1:1; 50 ml) and water (150 ml)
  7. customdried at 40° C. in vacuo

Sources & evidence

ORD record
ord-9367ccf5077f4368aacc901d7d0f4180
Source dataset
uspto-grants-1994_07
Patent number
US05332831

Reaction notes

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