Chloroform → HCID 13175694, compound

HRID 1981971Notes

Reaction equation

HRID 1981971 reaction equation
O.O.O.O.O.O.O.O.O.[S-2:10].[Na+].[Na+].[Cl:13][C:14]1[CH:15]=[CH:16][C:17]2[N:23]([CH2:24][CH2:25]Cl)[CH:22]([CH2:27]Cl)[CH2:21][N:20]=[C:19]([C:29]3[O:30][CH:31]=[CH:32][CH:33]=3)[C:18]=2[CH:34]=1.ClC1CN=C(C2OC=CC=2)C2C=CC(Cl)=CC=2N(CCCl)C1.C(Cl)(Cl)Cl>O.O1CCOCC1>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]2[N:23]3[CH2:24][CH2:25][S:10][CH2:27][CH:22]3[CH2:21][N:20]=[C:19]([C:29]3[O:30][CH:31]=[CH:32][CH:33]=3)[C:18]=2[CH:34]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 73972Sodium sulfide nonahydrateHCID 13175737HCID 13175737, compoundHCID 233183303,9-Dichloro-1-(beta-chloroethyl)-6-(2-furyl)-1,2,3,4-tetrahydro-1,5-benzodiazocine

Product 1

HCID 13175694HCID 13175694, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

8.5 g of disodium sulphide nonahydrate in 75 ml of water are added to a solution of 12.7 g of 7-chloro-1-(β-chloroethyl)-2-chloromethyl-5-(2-furyl)-2,3-dihydro-1H-1,4-benzodiazepine (or a mixture of this compound and the isomeric 3,9-dichloro-1-(β-chloroethyl)-6-(2-furyl)-1,2,3,4-tetrahydro-1,5-benzodiazocine (for the preparation see Example 5B) in 150 ml of dioxane, and the reaction mixture is heated under reflux for 5 hours. After the solvent has been stripped off in vacuo, the crude reaction product is isolated from chloroform and is then purified by chromatography on aluminium oxide of activity level II, using methylene chloride, and crystallised from ether. 9.7 g of 1,2,4,4a-tetrahydro-9-chloro-7-(2-furyl)-5H-[1,4]-thiazino[4,3-a][1,4]benzodiazepine are obtained. Melting point: 138° to 140° C.

Workup

  1. additiona mixture of this compound
  2. temperaturethe reaction mixture is heated
  3. temperatureunder reflux for 5 hours
  4. customthe crude reaction product
  5. customis then purified by chromatography on aluminium oxide of activity level II
  6. customcrystallised from ether

Sources & evidence

ORD record
ord-72a7d443809a4af8a806a1d909998ac7
Source dataset
uspto-grants-1986_06
Patent number
US04594436

Reaction notes

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