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Acetic Acid → (+/-)-5-(7-Chloro-2-(1,3,4-thiadiazolylthio)-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-yl)-1-methyl-2,4(1H,3H)-pyrimidinedione

HRID 324508
Notes
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Reaction equation

HRID 324508 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:11]=[CH:10][C:9]3[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:8]=3[CH:7]([C:17]3[C:18](=[O:25])[NH:19][C:20](=[O:24])[N:21]([CH3:23])[CH:22]=3)[C:5]=2[N:6]=1.[SH:26][C:27]1[S:28][CH:29]=[N:30][N:31]=1.[H-].[Na+].C(O)(=O)C>CN(C)C=O.O>[Cl:16][C:13]1[CH:14]=[CH:15][C:8]2[CH:7]([C:17]3[C:18](=[O:25])[NH:19][C:20](=[O:24])[N:21]([CH3:23])[CH:22]=3)[C:5]3[N:6]=[C:2]([S:26][C:27]4[S:28][CH:29]=[N:30][N:31]=4)[S:3][C:4]=3[CH:11]=[CH:10][C:9]=2[CH:12]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 70113243(+/-)-5-(2,7-Dichloro-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-yl)-1-methyl-2,4(1H,3H)-pyrimidinedioneHCID 178527973HCID 178527973, compound

Product 1

HCID 70113211(+/-)-5-(7-Chloro-2-(1,3,4-thiadiazolylthio)-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-yl)-1-methyl-2,4(1H,3H)-pyrimidinedione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

To a mixture of the product from example 44 step (viii) (0.20 g) and 2-mercapto-1,3,4-thiadiazole (0.120 g) in dry dimethylformamide (2 ml) was added 60% sodium hydride (0.041 g). The mixture was stirred for 16 h then heated at 55° C. for 24 h. The reaction mixture was diluted with water and neutralised by the addition of acetic acid. The aqueous was extracted with dichloromethane and the combined organic extracts were dried (MgSO4). The solvent was removed under reduced pressure and the residue purified by flash chromatography eluting with dichloromethane/5% ethanol.

Workup

  1. extractionThe aqueous was extracted with dichloromethane
  2. dry with materialthe combined organic extracts were dried (MgSO4)
  3. customThe solvent was removed under reduced pressure
  4. customthe residue purified by flash chromatography
  5. washeluting with dichloromethane/5% ethanol

Sources & evidence

ORD record
ord-41069b28a3854e989e612c79d92963e9
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06218376B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes