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

HRID 1532559Notes

Reaction equation

HRID 1532559 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 Na2SO, 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 Na2SO
  5. customevaporated down

Sources & evidence

ORD record
ord-c904efaffff64b9785a9913fb18980a3
Source dataset
uspto-grants-2001_03
Patent number
US06204222B1

Reaction notes

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