Acetic Anhydride → HCID 18993030, compound

HRID 375519Notes

Reaction equation

HRID 375519 reaction equation
[NH2:1][C:2]1[O:3][CH:4]=[C:5]([CH3:9])[C:6]=1[C:7]#[N:8].[CH2:10](OC(OCC)OCC)C.C(OC(=O)C)(=O)C.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][NH2:36])=[CH:30][CH:29]=1.C([O-])(=O)C.[Na+]>O.C(O)(=O)C>[CH3:9][C:5]1[C:6]2[C:7]([NH:36][CH2:35][CH2:34][C:31]3[CH:32]=[CH:33][C:28]([Cl:27])=[CH:29][CH:30]=3)=[N:8][CH:10]=[N:1][C:2]=2[O:3][CH:4]=1

Participants

8

Reactant 5

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 674302-(4-Chlorophenyl)ethylamineHCID 517045Sodium AcetateHCID 110188532-AMINO-4-METHYL-3-FURONITRILE

Product 1

HCID 18993030HCID 18993030, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 4.0 g of 2-amino-3-cyano-4-methylfuran, 3 cc of triethylorthoformate, and 0.05 cc of acetic anhydride was heated to 135° C. for three hours. Then 5 g of 2-(4-chlorophenyl)ethylamine, 5 cc of glacial acetic acid, and 3.2 g of sodium acetate were added to the reaction mixture. The temperature of the mixture was maintained at 135° C. for three additional hours, after which the mixture was cooled, treated with water and extracted with dichloromethane. The organic phase was then concentrated and washed with water. The solids were extracted from the organic phase with large volumes of ether, which were combined and concentrated to provide 1.07 g of product. M. P. 140° C.

Workup

  1. temperatureThe temperature of the mixture was maintained at 135° C. for three additional hours
  2. temperatureafter which the mixture was cooled
  3. extractionextracted with dichloromethane
  4. concentrationThe organic phase was then concentrated
  5. washwashed with water
  6. extractionThe solids were extracted from the organic phase with large volumes of ether, which
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f43d2e5d48eb4f919148ad48efc34c84
Source dataset
uspto-grants-1996_01
Patent number
US05486516

Reaction notes

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