Dimethylcyanamide → HCID 18434203, compound

HRID 1636760Notes

Reaction equation

HRID 1636760 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[S:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)=[CH:13][CH:14]=2)=[O:9])=[CH:4][CH:3]=1.[Br:22]N1C(=O)CCC1=O.C(#N)N(C)C>C(Cl)(Cl)(Cl)Cl>[Br:22][CH2:21][C:18]1[CH:17]=[CH:16][C:15]([C:12]2[S:11][C:10]([C:8]([C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=3)=[O:9])=[CH:14][CH:13]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 15112DimethylcyanamideHCID 67184N-bromobutanimideHCID 18434246HCID 18434246, compound

Product 1

HCID 18434203HCID 18434203, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

0.5 g of (4-bromophenyl)-(5-p-tolyl-thiophen-2-yl)-methanone and 262 mg of N-bromosuccinimide in 20 ml of carbon tetrachloride are held at reflux for 19 hrs. after the addition of a spatula tip of azaisobutyronitrile, concentrated and the residue is chromatographed on silica gel (methylene chloride/hexane). 517 mg of [5-(4-bromomethyl-phenyl)-thiophen-2-yl]-4-bromophenyl-methanone, m.p. 184° C. (decomposition), are isolated.

Workup

  1. temperatureat reflux for 19 hrs
  2. concentrationconcentrated
  3. customthe residue is chromatographed on silica gel (methylene chloride/hexane)

Sources & evidence

ORD record
ord-5e8eaa7a1e8c44308eca3943633eea5e
Source dataset
uspto-grants-2000_03
Patent number
US06034275

Reaction notes

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