4,5,6,7-Tetrahydro-5-methyl-1,3-isobenzofurandione → HCID 22013583, compound

HRID 398806Notes

Reaction equation

HRID 398806 reaction equation
[Cl:1][CH:2]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:3][C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][C:10]=1[Cl:11])[NH2:7].[CH3:17][CH:18]1[CH2:28][CH2:27][C:21]2[C:22]([O:24][C:25](=O)[C:20]=2[CH2:19]1)=[O:23]>>[Cl:11][C:10]1[CH:9]=[CH:8][C:6]([N:7]2[C:25](=[O:24])[C:20]3[CH2:19][CH:18]([CH3:17])[CH2:28][CH2:27][C:21]=3[C:22]2=[O:23])=[CH:5][C:4]=1[CH2:3][CH:2]([Cl:1])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

3

Reactant 2

HCID 1181314,5,6,7-Tetrahydro-5-methyl-1,3-isobenzofurandioneHCID 22013609HCID 22013609, compound

Product 1

HCID 22013583HCID 22013583, compound

Procedure

2.60 g of 3-(2-chloro-2-ethoxycarbonyleth-1-yl)-4-chloroaniline and 1.65 g of 4-methyl-3,4,5,6-tetrahydrophthalic anhydride were refluxed for 6 hours. After the mixture had been cooled and evaporated down, the residue was taken up in ethyl acetate and the solution was washed three times with water. The organic phase was dried over Na2SO4 and then evaporated down. Yield 3.0 g (75%); 1H-NMR (in d6 -DMSO/TMS): δ [ppm]=0.96 (d; 3H), 1.05 (t; 3H), 1.64-2.08 (m; 3H), 2.15-2.70 (m; 4H), 3.20-3.55 (m; 2H), 4.14 (q; 2H), 4.78 (dd; 1H), 7.26 (d; 1H), 7.34 (s; 1H), 7.55 (d; 1H).

Workup

  1. temperatureAfter the mixture had been cooled
  2. customevaporated down
  3. washthe solution was washed three times with water
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customevaporated down

Sources & evidence

ORD record
ord-9ba5b09b1c564d40b721607a1f089433
Source dataset
uspto-grants-1998_10
Patent number
US05817603

Reaction notes

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