Chloroacetone → 7-Chloro-2-[(2-chloro-1-methylethylidene)-hydrazino]-5-(o-chlorophenyl)-3H-1,4-benzodiazepine

HRID 328097Notes

Reaction equation

HRID 328097 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([NH:12][NH2:13])[CH2:9][N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:20])[C:6]=2[CH:21]=1.O1CCCC1.[Cl:27][CH2:28][C:29](=O)[CH3:30].CO.C1C=CC=CC=1>CCOCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([NH:12][N:13]=[C:29]([CH3:30])[CH2:28][Cl:27])[CH2:9][N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:20])[C:6]=2[CH:21]=1

Participants

6

Reactant 4

HCID 6571ChloroacetoneHCID 8028TetrahydrofuranHCID 123908757-Chloro-5-(2-chlorophenyl)-2-hydrazinyl-3H-1,4-benzodiazepineHCID 21927730Benzene methanol

Product 1

HCID 536320907-Chloro-2-[(2-chloro-1-methylethylidene)-hydrazino]-5-(o-chlorophenyl)-3H-1,4-benzodiazepine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3.19 g. (0.01 mole) of 7-chloro-5-(o-chlorophenyl)-2-hydrazino-3H-1,4-benzodiazepine and 100 ml. of tetrahydrofuran, under nitrogen, was cooled to 0° C. and 1 ml. of chloropropanone was slowly added with stirring. The mixture was allowed to warm to room temperature; after one-half hour all the solid had dissolved. After stirring for a total of 2 hours, thin layer chromatography (SiO2, 20% methanol/benzene) showed essentially one spot. Evaporation at room temperature in vacuo gave a light brown gum which was dissolved in absolute ether and filtered. The solution was concentrated by a stream of N2 on a steam bath to a small volume and pentane was added. After cooling in the refrigerator, the resulting crystals were collected, washed with ether and pentane and dried, yielding 3.82 g. (97%) of 7-chloro-2-[(2-chloro-1-methylethylidene)hydrazinoe]-5-(o-chlorophenyl)-3H-1,4-benzodiazepine.

Workup

  1. additionA mixture of 3.19 g
  2. dissolutionafter one-half hour all the solid had dissolved
  3. customEvaporation at room temperature in vacuo
  4. customgave a light brown gum which
  5. filtrationfiltered
  6. concentrationThe solution was concentrated by a stream of N2 on a steam bath to a small volume and pentane
  7. additionwas added
  8. temperatureAfter cooling in the refrigerator
  9. customthe resulting crystals were collected
  10. washwashed with ether and pentane
  11. customdried
  12. customyielding 3.82 g

Sources & evidence

ORD record
ord-28ab528b54104157a3c36fae5c934072
Source dataset
uspto-grants-1977_04
Patent number
US04016165

Reaction notes

Loading…