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Acetic Anhydride → 9-acetoxymethyl-2-chloro-4-(o-chlorophenyl)-6H-thieno[3,2-f]-s-triazolo[4,3-a][1,4]-diazepine

HRID 262990
Notes
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Reaction equation

HRID 262990 reaction equation
[Cl:1][C:2]1[S:11][C:10]2[N:9]3[C:12]([CH2:15][OH:16])=[N:13][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[Cl:23])[C:4]=2[CH:3]=1.[C:24](OC(=O)C)(=[O:26])[CH3:25]>N1C=CC=CC=1>[C:24]([O:16][CH2:15][C:12]1[N:9]2[C:10]3[S:11][C:2]([Cl:1])=[CH:3][C:4]=3[C:5]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])=[N:6][CH2:7][C:8]2=[N:14][N:13]=1)(=[O:26])[CH3:25]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 213176872-chloro-4-(o-chlorophenyl)-6H-thieno[3,2-f]-s-triazolo[4,3-a][1,4]diazepine-9-methanol

Product 1

HCID 213177049-acetoxymethyl-2-chloro-4-(o-chlorophenyl)-6H-thieno[3,2-f]-s-triazolo[4,3-a][1,4]-diazepine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
30 °C

Procedure

1 g of 2-chloro-4-(o-chlorophenyl)-6H-thieno[3,2-f]-s-triazolo[4,3-a][1,4]diazepine-9-methanol is dissolved in 10 ml of absolute pyridine and treated with 1 ml of acetic anhydride. The solution is maintained at 30° C. for 15 hours and then evaporated under vacuum. The residue is partitioned between methylene chloride and water. The organic phase is washed with saturated sodium chloride solution, dried over sodium sulphate and evaporated. By recrystallization of the residue from ethyl acetate, there is obtained 9-acetoxymethyl-2-chloro-4-(o-chlorophenyl)-6H-thieno[3,2-f]-s-triazolo[4,3-a][1,4]-diazepine of melting point 191°-193° C.

Workup

  1. customevaporated under vacuum
  2. customThe residue is partitioned between methylene chloride and water
  3. washThe organic phase is washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customBy recrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-b3b5b636b9ac47b693000d6307d947e7
Source dataset
uspto-grants-1979_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04155913

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes