Water → HCID 15573101, compound

HRID 224236Notes

Reaction equation

HRID 224236 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH2:15][SH:16])=[N:13][N:14]=[C:10]3[CH2:9][N:8]=[C:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])[C:6]=2[CH:24]=1.Br[S:26][N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.O>C(Cl)Cl.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH2:15][S:16][S:26][N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)=[N:13][N:14]=[C:10]3[CH2:9][N:8]=[C:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])[C:6]=2[CH:24]=1

Participants

6

Reactant 3

HCID 962WaterHCID 14914423HCID 14914423, compoundHCID 15573095HCID 15573095, compound

Product 1

HCID 15573101HCID 15573101, compoundYield 124.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-chloro-1-(mercaptomethyl)-6-(2-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine (1.5 g) in methylene chloride (20 ml) is added a solution of 4-(bromothio)morpholine (prepared from 0.47 g of dimorpholinodisulfide) in chloroform at -13° to -20° C., and the resultant mixture is stirred for 1.5 hours. The reaction mixture is mixed with water. The methylene chloride layer is separated, dried and evaporated to remove the solvent. The residue is crystallized from ether and filtered to give 8-chloro-1-(morpholinodithio)methyl-6-(2-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine (1.45 g) as crystals. This material is recrystallized from ethanol to give crystals melting at 149°-155° C. (decomp.).

Workup

  1. customThe methylene chloride layer is separated
  2. customdried
  3. customevaporated
  4. customto remove the solvent
  5. customThe residue is crystallized from ether
  6. filtrationfiltered

Sources & evidence

ORD record
ord-eeb171495e0149d483ffa33f39d122ec
Source dataset
uspto-grants-1980_11
Patent number
US04231930

Reaction notes

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