Chloranil → HCID 12658710, compound

HRID 427035Notes

Reaction equation

HRID 427035 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([NH:6][C:7]2[CH2:8][S:9][CH2:10][C:11]=2[C:12]#[N:13])=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1.C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([NH:6][C:7]2[C:11]([C:12]#[N:13])=[CH:10][S:9][CH:8]=2)=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1

Participants

4

Reactant 2

HCID 8371ChloranilHCID 126587034-(4-Chloro-2-nitroanilino)-2,5-dihydrothiophene-3-carbonitrile

Product 1

HCID 12658710HCID 12658710, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

3-(4-Chloro-2-nitroanilino)-2,5-dihydrothiophene-4-nitrile (14,09 g, 0.05 mol) dissolved in xylene (150 ml) was added to a solution of chloranil (12.3 g, 0.05 mol) in hot xylene (100 ml). The mixture was allowed to reflux for two hours. After cooling, the xylene was evaporated off under vacuum to leave a red-brown solid which was triturated with methanol to give a brick-red solid. The solid was recrystallised from hot methanol to give red crystals which were filtered off, washed with methanol and dried at 50° C. under vacuum. The dried product so obtained was the title compound, m.p. 214° C.

Workup

  1. temperatureto reflux for two hours
  2. temperatureAfter cooling
  3. customthe xylene was evaporated off under vacuum
  4. customto leave a red-brown solid which
  5. customwas triturated with methanol
  6. customto give a brick-red solid
  7. customThe solid was recrystallised from hot methanol
  8. customto give red crystals which
  9. filtrationwere filtered off
  10. washwashed with methanol
  11. customdried at 50° C. under vacuum
  12. customThe dried product so obtained

Sources & evidence

ORD record
ord-4a72f3ad5e8d4c58b075f5cae5491ad0
Source dataset
uspto-grants-1979_10
Patent number
US04172831

Reaction notes

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