Lawesson's reagent → 9-Bromo-benzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6(7H)-thione

HRID 703434Notes

Reaction equation

HRID 703434 reaction equation
[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]3[CH:17]=[CH:16][C:15]4[C:7]3=[C:8]([CH:12]=[CH:13][CH:14]=4)[C:9](=O)[NH:10][C:4]=2[CH:3]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:29]2)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]3[CH:17]=[CH:16][C:15]4[C:7]3=[C:8]([CH:12]=[CH:13][CH:14]=4)[C:9](=[S:29])[NH:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 138232869-bromobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6(7H)-one

Product 1

HCID 151325389-Bromo-benzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6(7H)-thioneYield 71.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 9-bromobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6(7H)-one (12.8 g), 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (8.3 g), and toluene (500 ml) was refluxed for 2 hrs. The reaction mixture was allowed to stand overnight at room temperature. The precipitate was collected, washed with hexane, and dried overnight under vacuum at 40° C. to provide 9.6 g, (71.5%) of product. Recrystallization from chloroform gave the analytical sample, mp 214°-215° C.

Workup

  1. temperaturewas refluxed for 2 hrs
  2. customThe precipitate was collected
  3. washwashed with hexane
  4. customdried overnight under vacuum at 40° C.

Sources & evidence

ORD record
ord-88d5cc5babc549de801b8e65be79d4b5
Source dataset
uspto-grants-1991_01
Patent number
US04983601

Reaction notes

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