Acetic Anhydride → HCID 12925977, compound

HRID 894613Notes

Reaction equation

HRID 894613 reaction equation
[C:1]([NH:4][C:5]1[C:6]([Cl:22])=[CH:7][C:8]([C:18](OC)=[O:19])=[C:9]([O:11][CH:12]2[CH2:17][CH2:16][O:15][C:13]2=[O:14])[CH:10]=1)(=[O:3])[CH3:2].[C:23](OC(=O)C)(=[O:25])[CH3:24]>C(N(CC)CC)C>[C:23]([N:4]([C:1](=[O:3])[CH3:2])[C:5]1[C:6]([Cl:22])=[CH:7][C:8]2[C:18](=[O:19])[C:12]3([CH2:17][CH2:16][O:15][C:13]3=[O:14])[O:11][C:9]=2[CH:10]=1)(=[O:25])[CH3:24]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 12925954alpha-[(5-Acetylamino-4-chloro-2-methoxycarbonylphenyl)oxy]-gamma-butyrolactone

Product 1

HCID 12925977HCID 12925977, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 23 g. of α-[(5-acetylamino-4-chloro-2-methoxycarbonylphenyl)oxy]-γ-butyrolactone, 46 ml. of triethylamine and 230 ml. of acetic anhydride was heated at 120° C. for 5 hours. The solvents were evaporated off under reduced pressure, then the residue was poured into ice-water. The precipitating crystals were collected by filtration, washed with water and dried, followed by recrystallization from ethyl acetate to give 6-diacetylamino-5-chloro-4',5'-dihydrospiro[benzo[b]furan-2(3H), 3'(2'H)-furan]-2',3-dione melting at 181°-185° C. Yield 6.8 g.

Workup

  1. additionA mixture of 23 g
  2. customThe solvents were evaporated off under reduced pressure
  3. additionthe residue was poured into ice-water
  4. filtrationThe precipitating crystals were collected by filtration
  5. washwashed with water
  6. customdried
  7. customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-5a18b612b4f74cafa6646bbe3476d4dc
Source dataset
uspto-grants-1981_08
Patent number
US04284644

Reaction notes

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