Acetonitrile → HCID 12517757, compound

HRID 1391353Notes

Reaction equation

HRID 1391353 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C:3]1=O.P(Cl)(Cl)(Cl)=O.N[C:14]1[CH:27]=[CH:26][C:25]2[C:24](=[O:28])[C:23]3[C:18](=[CH:19][CH:20]=[C:21](N)[CH:22]=3)[C:17](=[O:30])[C:16]=2[CH:15]=1.[OH-].[Na+].CC#[N:35]>>[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C:3]1=[N:35][C:15]1[C:16]2[C:17](=[O:30])[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:24](=[O:28])[C:25]=2[CH:26]=[CH:27][CH:14]=1

Participants

6

Reactant 5

HCID 6342AcetonitrileHCID 85572,6-DiaminoanthraquinoneHCID 13387N-methyl-2-pyrrolidoneHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychloride

Product 1

HCID 12517757HCID 12517757, compound

Procedure

To a solution of 34.5 g of 1-methyl-2-pyrrolidinone in 150 ml. of CH3CN was added 18.4 g of phosphorous oxychloride at 5°-10° C. The mixture was stirred at room temperature for 1 hour. To the mixture was added 11.9 g of 2,6-diaminoanthraquinone. The resulting mixture was stirred at 60° C. for 10 hours, poured into 1000 ml of ice-water and basified with 5N NaOH. Reddish crystals thus obtained were collected by filtration and washed with water. Recrystallization from methyl cellusolve gave 14.0 g of reddish crystals, mp 267°-269° C.

Workup

  1. stirringThe resulting mixture was stirred at 60° C. for 10 hours
  2. customReddish crystals thus obtained
  3. filtrationwere collected by filtration
  4. washwashed with water
  5. customRecrystallization from methyl cellusolve

Sources & evidence

ORD record
ord-635f3fb6b775429cafd84a2c53d3c18c
Source dataset
uspto-grants-1979_02
Patent number
US04141992

Reaction notes

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