Ethanol → HCID 178442496, compound

HRID 374597Notes

Reaction equation

HRID 374597 reaction equation
[CH2:1]([C:7]1[CH2:11][C:10](=[O:12])[O:9][N:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:13]([C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH3:26]CO>C(OCC)(OCC)OCC>[CH2:13]([C:19]1[CH:20]=[CH:21][C:22]([NH:23]/[CH:26]=[C:11]2/[C:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[N:8][O:9][C:10]/2=[O:12])=[CH:24][CH:25]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 702EthanolHCID 363824-HexylanilineHCID 45099350HCID 45099350, compound

Product 1

HCID 178442496HCID 178442496, compound

Reagents, catalysts & solvents 1

HCID 31214Ethyl orthoformateSolvent

Procedure

1.7 g of 3-n-hexylisoxazol-5(4H)-one (prepared in accordance with Example 3) are dissolved in 10 ml of triethyl orthoformate and heated at 80° C. for 2 hours together with 2.65 g of p-hexylaniline. The dark reaction solution is concentrated and recrystallized in 100 ml of hexane. 1.8 g (50% of theory) of the above-named crystalline compound are obtained. M.p. 88°-90° C., UV (EtOH): 356 nm (ε=26469). This compound is especially suitable as a UV A filter.

Workup

  1. concentrationThe dark reaction solution is concentrated
  2. customrecrystallized in 100 ml of hexane
  3. custom1.8 g (50% of theory) of the above-named crystalline compound are obtained

Sources & evidence

ORD record
ord-f60b3bc5235047e99151116771104e08
Source dataset
uspto-grants-1996_01
Patent number
US05481001

Reaction notes

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