Thionyl Chloride → HCID 21432799, compound

HRID 2399144Notes

Reaction equation

HRID 2399144 reaction equation
[F: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]([Cl:19])[CH:17]=[CH:18][C:13]=2[N:12]2[N:20]=[C:21]([C:23]([OH:25])=O)[N:22]=[C:11]2[CH2:10][N:9]=1.S(Cl)([Cl:28])=O>>[F: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]([Cl:19])[CH:17]=[CH:18][C:13]=2[N:12]2[N:20]=[C:21]([C:23]([Cl:28])=[O:25])[N:22]=[C:11]2[CH2:10][N:9]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 12404527HCID 12404527, compound

Product 1

HCID 21432799HCID 21432799, compound

Procedure

An amount of 3.63 g (0.010 mole) of 6-(o-fluorophenyl)-8-chloro-4H-s-triazolo[1,5-a][1,4]benzodiazepine-2-carboxylic acid is refluxed with 60 ml of thionyl chloride for two hours. The clear yellow solution is concentrated at 40° in vacuo and, to effect the total removal of thionyl chloride, the residue dissolved in 50 ml of abs. toluene and again concentrated by evaporation to obtain as residue crude 6-(o-fluorophenyl)-8-chloro-4H-s-triazolo[1,5-a][1,4]benzodiazepine-2-carbonyl chloride. It can be optionally recrystallised from dioxane and has then a M.P. of 196°-198° (decomposition).

Workup

  1. concentrationThe clear yellow solution is concentrated at 40° in vacuo
  2. customthe total removal of thionyl chloride
  3. dissolutionthe residue dissolved in 50 ml of abs
  4. concentrationtoluene and again concentrated by evaporation

Sources & evidence

ORD record
ord-0807b74e5243490893261b3551579798
Source dataset
uspto-grants-1977_05
Patent number
US04027029

Reaction notes

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