Acetic Anhydride → HCID 10612833, compound

HRID 1884338Notes

Reaction equation

HRID 1884338 reaction equation
[NH2:1][C:2]1[N:3]([C:10]2[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=2[CH3:18])[CH:4]=[C:5]([CH3:9])[C:6]=1[C:7]#[N:8].[C:19](OC(=O)C)(=[O:21])[CH3:20]>C(O)(=O)C>[C:7]([C:6]1[C:5]([CH3:9])=[CH:4][N:3]([C:10]2[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=2[CH3:18])[C:2]=1[NH:1][C:19](=[O:21])[CH3:20])#[N:8]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 10537962HCID 10537962, compound

Product 1

HCID 10612833HCID 10612833, compoundYield 105.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of the purified compound of step A (3.000 g, 12.54 mmol) and acetic anhydride (1.410 g, 1.31 ml, 13.82 mmol) in 3 ml of acetic acid was refluxed for 45 minutes, cooled and poured onto crushed ice and extracted with ethyl acetate. The organic layer was neutralized, dried and concentrated to give 3.71 g (105%) of dark-pink glass foam. 1H NMR (CDCl3) □ 1.95(s, 6H), 2.2(s, 3H), 2.32 (s, 3H), 6.2(s, 1H), 6.8(brs, 1H, NH), 6.9(s, 2H) ppm.

Workup

  1. temperaturewas refluxed for 45 minutes
  2. temperaturecooled
  3. additionpoured
  4. customonto crushed ice
  5. extractionextracted with ethyl acetate
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0b301b6b3cff43039b52a6d5622a6ad2
Source dataset
uspto-grants-2004_07
Patent number
US06765008B1

Reaction notes

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