Acetic Anhydride → HCID 20098370, compound

HRID 1165237Notes

Reaction equation

HRID 1165237 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([OH:20])=[C:6]([CH:19]=1)[C:7]([NH:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH:12]=[CH:13][NH:14]2)=[O:8].[C:21](OC(=O)C)(=[O:23])[CH3:22].[O:28]1CC[CH2:30][CH2:29]1>>[C:21]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][C:29](=[O:28])[CH3:30])=[C:6]([CH:19]=1)[C:7]([NH:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH:12]=[CH:13][NH:14]2)=[O:8])(=[O:23])[CH3:22]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 20098375HCID 20098375, compound

Product 1

HCID 20098370HCID 20098370, compound

Procedure

A suspension of 2.6 g of the product of Step A in 70 ml of tetrahydrofuran was cooled to 0° to 5° C. and then 4.7 ml of acetic anhydride were added. The mixture was held at room temperature for 3 hours and was then evaporated to dryness under reduced pressure at 50° C. The residue was taken up in a 1-1 mixture of chloroform-methanol and was filtered. The product was dried at 80° C. to obtain 2.7 g of 5-acetylamino-2-acetoxy-N-(1H-indol-4-yl)-benzamide melting at 263° C.

Workup

  1. temperaturewas cooled to 0° to 5° C.
  2. customwas then evaporated to dryness under reduced pressure at 50° C
  3. additionThe residue was taken up in a 1-1 mixture of chloroform-methanol
  4. filtrationwas filtered
  5. customThe product was dried at 80° C.

Sources & evidence

ORD record
ord-53b98cc2eea6445585a4beaaffcbf9d3
Source dataset
uspto-grants-1990_03
Patent number
US04908367

Reaction notes

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