Acetic Anhydride → HCID 131722267, compound

HRID 566275Notes

Reaction equation

HRID 566275 reaction equation
[Cl:1][C:2]1[S:11][C:10]2[N:9]3[CH2:12][CH:13](CO)[N:14]=[C:8]3[CH2:7][N:6]=[C:5]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[F:23])[C:4]=2[CH:3]=1.[C:24]([O:27]C(=O)C)(=[O:26])[CH3:25]>Cl(O)(=O)(=O)=O>[ClH:1].[Cl:1][C:2]1[S:11][C:10]2[N:9]3[CH2:12][CH:13]([CH2:25][C:24]([OH:27])=[O:26])[N:14]=[C:8]3[CH2:7][N:6]=[C:5]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[F:23])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 21265960HCID 21265960, compound

Product 1

HCID 131722267HCID 131722267, compound

Reagents, catalysts & solvents 1

HCID 24247Perchloric AcidCatalyst

Procedure

31 drops of perchloric acid (70%) were added to a suspension of 1.5 g of 2-chloro-4-(2-fluoro-phenyl)-8,9-dihydro-6H-imidazo[1,2-a]thieno-[3,2-f][1,4]diazepine-8-methanol in 31 ml of acetic anhydride until the starting product was completely in solution. After stirring at room temperature for 20 min. the solution was poured into sodium carbonate/ice/dichloromethane and stirred at room temperature for 1 h. After extraction the dichloromethane extracts were dried with sodium sulphate, filtered and evaporated to dryness in a vacuum. The residue was dried in a high vacuum for 2 h., dissolved in 30 ml of acetone, treated with 52 g of 1.6% hydrochloric acid gas in diethyl ether, evaporated in a vacuum (223 mbar) and crystallized from acetone. After crystallization from acetone there was obtained 1 g of methyl[2-chloro-4-(2-fluoro-phenyl)-8,9-dihydro-6H-imidazo[1,2-a]thieno[3,2-f][1,4]diazepin-8-yl-acetate-hydrochloride of m.p. 126-129° C. (dec., strongly hygroscopic).

Workup

  1. stirringstirred at room temperature for 1 h
  2. extractionAfter extraction the dichloromethane extracts
  3. dry with materialwere dried with sodium sulphate
  4. filtrationfiltered
  5. customevaporated to dryness in a vacuum
  6. customThe residue was dried in a high vacuum for 2 h.
  7. dissolutiondissolved in 30 ml of acetone
  8. additiontreated with 52 g of 1.6% hydrochloric acid gas in diethyl ether
  9. customevaporated in a vacuum (223 mbar)
  10. customcrystallized from acetone
  11. customAfter crystallization from acetone

Sources & evidence

ORD record
ord-2a0c83af8eb647c2a8fb9f9e1052344e
Source dataset
uspto-grants-2001_01
Patent number
US06174881B1

Reaction notes

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