Acetic Anhydride → HCID 9935016, compound

HRID 323655Notes

Reaction equation

HRID 323655 reaction equation
[Cl:1][C:2]1[C:3]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=[C:4]2[C:22]3[CH2:21][CH2:20][NH:19][CH2:18][C:17]=3[S:16][C:5]2=[N:6][C:7]=1[CH2:8][N:9]1[C:13](=[O:14])[CH2:12][CH2:11][C:10]1=[O:15].C(N(CC)CC)C.[O:38]1CC[CH2:40][CH2:39]1.C(OC(=O)C)(=O)C>C(OCC)(=O)C>[C:39]([N:19]1[CH2:20][CH2:21][C:22]2[C:4]3[C:5]([S:16][C:17]=2[CH2:18]1)=[N:6][C:7]([CH2:8][N:9]1[C:10](=[O:15])[CH2:11][CH2:12][C:13]1=[O:14])=[C:2]([Cl:1])[C:3]=3[C:23]1[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=1)(=[O:38])[CH3:40]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 9933006HCID 9933006, compound

Product 1

HCID 9935016HCID 9935016, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution mixture containing the compound obtained in Example 1 (1 g), triethylamine (343 mg) and tetrahydrofuran (50 ml) was added acetic anhydride (254 mg) while cooling with ice. After stirring for 2 hours at room temperature, the reaction solution was concentrated under reduced pressure. The residue thus obtained was dissolved in ethyl acetate (50 ml), washed with water, dried (MgSO4) and then the solvent was distilled off to obtain the title compound (582 mg, 53%). The product was recrystallized from tetrahydrofuran. A colorless prism crystal. M.p. 266 to 267° C.

Workup

  1. temperaturewhile cooling with ice
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. customThe residue thus obtained
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-e4829621f0c046fb9012baf085e022db
Source dataset
uspto-grants-2001_04
Patent number
US06214838B1

Reaction notes

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