Potassium Carbonate → HCID 11060875, compound

HRID 1531316

Reaction equation

HRID 1531316 reaction equation
[CH:1]1([O:6][C:7]2[C:14]([O:15][CH3:16])=[CH:13][C:10]([CH:11]=O)=[CH:9][C:8]=2[O:17][CH3:18])[CH2:5][CH2:4][CH2:3][CH2:2]1.[N:19]1[S:20][N:21]=[C:22]2[CH:27]=[C:26]([CH:28]([CH2:34][C:35]([C:37]3[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=3)=[O:36])[C:29]([O:31]CC)=[O:30])[CH:25]=[CH:24][C:23]=12.N1SN=C2C=C(CC(OCC)=O)C=CC=12.C(=O)([O-])[O-].[K+].[K+].NC1C=C(CC(OCC)=O)C=CC=1N.S(=NC1C=CC=CC=1)=O.[Na]>CC(C)=O.C1(C)C=CC=CC=1.C(O)C.C(O)(=O)C>[N:19]1[S:20][N:21]=[C:22]2[CH:27]=[C:26]([C:28]3[C:29](=[O:30])[O:31][C:35]([OH:36])([C:37]4[CH:38]=[CH:39][C:40]([O:43][CH3:44])=[CH:41][CH:42]=4)[C:34]=3[CH2:11][C:10]3[CH:13]=[C:14]([O:15][CH3:16])[C:7]([O:6][CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)=[C:8]([O:17][CH3:18])[CH:9]=3)[CH:25]=[CH:24][C:23]=12

Participants

12

Reactant 7

HCID 11430Potassium CarbonateHCID 70739Benzenamine, N-sulfinyl-HCID 5360545SodiumHCID 10926758Ethyl 2-(2,1,3-benzothiadiazol-5-yl)-4-(4-methoxyphenyl)-4-oxobutanoateHCID 11127870Ethyl 2-(benzo[c][1,2,5]thiadiazol-5-yl)acetate2×HCID 117916034-Cyclopentyloxy-3,5-dimethoxybenzaldehydeHCID 12986345Ethyl 2-(3,4-diaminophenyl)acetate

Product 1

HCID 11060875HCID 11060875, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

0.368 g of 4-cyclopentyloxy-3,5-dimethoxybenzaldehyde (“A”) and 0.52 g of ethyl 2-(2,1,3-benzothiadiazol-5-yl)-4-(4-methoxyphenyl)-4-oxobutanoate, m.p. 89° (obtainable by reaction of 5.5 g of ethyl 2-(2,1,3-benzothiadiazol-5-yl)acetate with 5.5 g of 2′-bromo-4-methoxyacetophenone and 4 g of potassium carbonate in 200 ml of acetone, 18 hours under reflux; ethyl 2-(2,1,3-benzothiadiazol-5-yl)acetate, m.p. 40-41° is obtained by reaction of 24.3 g of ethyl 3,4-diaminophenylacetate and 26.9 ml of thionylaniline in 80 ml of toluene, 4 hours under reflux) are added to a solution of 34 mg of sodium in 10 ml of ethanol and the mixture is heated under reflux for one hour. After addition of 1.4 ml of acetic acid, it is heated for a further 16 hours. The solvent is removed and the residue is worked up in the customary manner. 3-(2,1,3-Benzothiadiazol-5-yl)-4-(4-cyclopentyloxy-3,5-dimethoxy-benzyl)-5-hydroxy-5-(4-methoxyphenyl)-5H-furan-2-one is obtained, FAB 575.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for one hour
  3. temperatureis heated for a further 16 hours
  4. customThe solvent is removed

Sources & evidence

ORD record
ord-17a359feab954b548052de3d5d6c93ea
Source dataset
uspto-grants-2001_03
Patent number
US06197800B1

Linked notes

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