Chlorosuccinimide → HCID 14666717, compound

HRID 648545Notes

Reaction equation

HRID 648545 reaction equation
[C:1]1([C:7]2[C:20](=[O:21])[N:11]3[CH2:12][CH2:13][S:14][C:15]4[CH:19]=[CH:18][S:17][C:16]=4[C:10]3=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:22]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Cl:22][C:9]1[CH:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:20](=[O:21])[N:11]2[C:10]=1[C:16]1[S:17][CH:18]=[CH:19][C:15]=1[S:14][CH2:13][CH2:12]2

Participants

4

Reactant 2

HCID 31398Chlorosuccinimide2×HCID 14666683HCID 14666683, compound

Product 1

HCID 14666717HCID 14666717, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

4.95 g of 5,6-dihydro-9-phenyl-8H-pyrido[1,2-d]thieno[2,3-f][1,4]thiazepin-8-one were added under argon to 2.35 g of N-chlorosuccinimide in 50 ml of carbon tetrachloride. The mixture was stirred at room temperature for 2.5 hours, treated with an additional 0.21 g of N-chlorosuccinimide and stirred for an additional 1 hour. After evaporation in vacuo, the residue was chromatographed on silica gel. By recrystallization from acetonitrile, there was obtained 11-chloro-5,6-dihydro-9-phenyl-8H-pyrido[1,2-d]-thieno[2,3-f][1,4]thiazepin-8-one as yellow crystals of m.p. 179°.

Workup

  1. stirringstirred for an additional 1 hour
  2. customAfter evaporation in vacuo
  3. customthe residue was chromatographed on silica gel
  4. customBy recrystallization from acetonitrile

Sources & evidence

ORD record
ord-511ccb79eb994cfbbfe5729b0d4d26bf
Source dataset
uspto-grants-1988_04
Patent number
US04735940

Reaction notes

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