Ethanol → HCID 14851884, compound

HRID 1032774Notes

Reaction equation

HRID 1032774 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16](I)[S:17][C:13]=2[N:12]2[C:19]([CH3:22])=[N:20][N:21]=[C:11]2[CH2:10][N:9]=1.[Cl:23][C:24]1[CH:25]=[CH:26][C:27]2[O:32][CH2:31][C:30](=[O:33])[N:29]([CH2:34][C:35]#[CH:36])[C:28]=2[CH:37]=1.C(O)C>C(Cl)Cl>[Cl:23][C:24]1[CH:25]=[CH:26][C:27]2[O:32][CH2:31][C:30](=[O:33])[N:29]([CH2:34][C:35]#[C:36][C:16]3[S:17][C:13]4[N:12]5[C:19]([CH3:22])=[N:20][N:21]=[C:11]5[CH2:10][N:9]=[C:8]([C:3]5[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=5[Cl:1])[C:14]=4[CH:15]=3)[C:28]=2[CH:37]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 13666542HCID 13666542, compoundHCID 148519244-(2-chlorophenyl)-2-iodo-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine

Product 1

HCID 14851884HCID 14851884, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The titIe compound was prepared by coupling 4-(2-chlorophenyl)-2-iodo-9-methyl-6H-thieno [3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine with 6-chloro4-(2-propynyl)-2H-1,4-benzoxazin 3(4H)-one [ref. p. Rao et al. Indian J. Chem. 24 B, 1120 (1985)]as described in Example 37 but the reaction time was extended to 72 hours. The product was isolated by chromatography over the 100 -fold amount of silica gel (Merck 230-400 mesh) using 10% (v/v) of ethanol in methylene chloride. Crystallization of the residue obtained after evaporation of the combined clean fractions from ethyl acetate gave colorless crystals of 6-chloro-4-{3-[4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3 a][1,4]diazepin-2-yl]-2-propynyl}-2H-1,4-benzoxazin-3(4H)-one with m.p. 202°-205°.

Workup

  1. customThe titIe compound was prepared
  2. customThe product was isolated by chromatography over the 100 -fold amount of silica gel (Merck 230-400 mesh)
  3. customCrystallization of the residue
  4. customobtained
  5. customafter evaporation of the combined clean fractions from ethyl acetate

Sources & evidence

ORD record
ord-8a9364cd483c4120989fefb40cd27186
Source dataset
uspto-grants-1990_09
Patent number
US04959361

Reaction notes

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