Tetrahydrofuran → HCID 178456696, compound

HRID 2082783Notes

Reaction equation

HRID 2082783 reaction equation
Br[C:2]1[C:3]([N+:34]([O-:36])=[O:35])=[CH:4][C:5]2[N:11]=[C:10]([N:12]([CH2:14][CH2:15][CH3:16])[NH2:13])[CH:9]([CH2:17]C)[N:8]=[C:7]([C:19]3[CH:24]=[C:23](C(F)(F)F)[CH:22]=[C:21](OCCC)[CH:20]=3)[C:6]=2[CH:33]=1.C([N:39]([CH2:42]C)[CH2:40]C)C.C1C=CC(N=C(Cl)[Cl:52])=CC=1.O1[CH2:58][CH2:57]CC1>>[Cl-:52].[Cl:52][C:23]1[C:22]([CH2:57][CH3:58])=[CH:21][C:20]2[N:11]3[C:42]([NH:39][CH3:40])=[NH+:13][N:12]([CH2:14][CH2:15][CH3:16])[CH:10]3[CH:9]([CH3:17])[N:8]=[C:7]([C:6]3[CH:33]=[CH:2][C:3]([N+:34]([O-:36])=[O:35])=[CH:4][CH:5]=3)[C:19]=2[CH:24]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 12145Phenylimidocarbonyl chlorideHCID 54488386HCID 54488386, compound

Product 1

HCID 178456696HCID 178456696, compound

Procedure

A stirred mixture of 2.99 g. (0.01 mole) of 7-chloro-2-(1-methylhydrazino)-5-phenyl-3H-1,4-benzodiazepine (III), 3.12 ml. (0.022 mole) of triethylamine and 40 ml. of tetrahydrofuran is cooled in an ice bath and treated with a solution of phenylisocyanide dichloride (prepared as in Agew. Chem. Internat. Ed. 6, 649) in 20 ml. of tetrahydrofuran. The resulting mixture is allowed to warm slowly to room temperature and stand for about 18 hours. It is refluxed for about b 1 hour, cooled and concentrated to give 1-anilino-8-chloro-3-methyl-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepinium chloride (VIII).

Workup

  1. additionA stirred mixture of 2.99 g
  2. temperatureIt is refluxed for about b 1 hour
  3. temperaturecooled
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e079201707c64876887538efb5388a81
Source dataset
uspto-grants-1978_04
Patent number
US04082761

Reaction notes

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