Acetic Anhydride → 1-Acetoxymethyl-2-(4-methoxy-2-picolylmercapto)-1H-thieno[3,4-d]imidazole

HRID 231166Notes

Reaction equation

HRID 231166 reaction equation
[OH:1][CH2:2][N:3]1[C:7]2=[CH:8][S:9][CH:10]=[C:6]2[N:5]=[C:4]1[S:11][CH2:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][N:14]=1.[C:21](OC(=O)C)(=[O:23])[CH3:22]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:21]([O:1][CH2:2][N:3]1[C:7]2=[CH:8][S:9][CH:10]=[C:6]2[N:5]=[C:4]1[S:11][CH2:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][N:14]=1)(=[O:23])[CH3:22]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 141543311-Hydroxymethyl-2-(4-methoxy-2-picolylmercapto)1H-thieno[3,4-d]imidazole

Product 1

HCID 141543321-Acetoxymethyl-2-(4-methoxy-2-picolylmercapto)-1H-thieno[3,4-d]imidazole

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

1.3 g (4.2 mmol) of the title compound from Example 28 were dissolved in 25 ml of anhydrous pyridine, and 50 mg of 4-dimethylaminopyridine were added. Under a nitrogen atmosphere and while stirring, 6.3 ml acetic anhydride were added dropwise, and the mixture was stirred at room temperature for one hour. It was then poured onto ice water, extracted with methylene chloride, and the organic phase was dried over MgSO4 and concentrated in vacuo. The crystalline solid was recrystallized from ethanol. Melting point 111°-113° C.

Workup

  1. stirringthe mixture was stirred at room temperature for one hour
  2. additionIt was then poured onto ice water
  3. extractionextracted with methylene chloride
  4. dry with materialthe organic phase was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crystalline solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-78a64d4ef68b4ee0999c8357f465b6ba
Source dataset
uspto-grants-1989_07
Patent number
US04845118

Reaction notes

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