Acetone → HCID 135666743, compound

HRID 615657Notes

Reaction equation

HRID 615657 reaction equation
[C:1]([C:3]1[NH:4][N:5]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:6](=[O:25])[C:7]=1[N:8]=[N:9][C:10]1[CH:15]=[C:14]([S:16](O)(=[O:18])=[O:17])[C:13]([O:20][CH2:21][CH2:22][O:23][CH3:24])=[CH:12][CH:11]=1)#[N:2].CC(C)=O.P(Cl)(Cl)([Cl:38])=O>CN(C)C(=O)C>[C:1]([C:3]1[NH:4][N:5]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:6](=[O:25])[C:7]=1[N:8]=[N:9][C:10]1[CH:15]=[C:14]([S:16]([Cl:38])(=[O:18])=[O:17])[C:13]([O:20][CH2:21][CH2:22][O:23][CH3:24])=[CH:12][CH:11]=1)#[N:2]

Participants

5

Reactant 3

HCID 180AcetoneHCID 24813Phosphorus oxychlorideHCID 135666741HCID 135666741, compound

Product 1

HCID 135666743HCID 135666743, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a mixture of 51.0 g of the 3-cyano-4-[4-(2-methoxyethoxy)-5-sulfophenylazo]-1-phenyl-5-pyrazolone, 250 ml of acetone and 50 ml of phosphorus oxychloride was dropwise added 50 ml of N,N-dimethylacetamide at 50° C. or below. After the addition, the reaction mixture was stirred for about 1 hour and gradually poured into 1.0 l of ice water. The crystals precipitated were collected by filtration, washed with 100 ml of acetonitrile and dried by air. Thus, 46.7 g of 3-cyano-4-[4-(2-methoxyethoxy)-5-chlorosulfonylphenylazo]-1-phenyl-5-pyrazolone was obtained.

Workup

  1. customat 50° C. or below
  2. additionAfter the addition
  3. customThe crystals precipitated
  4. filtrationwere collected by filtration
  5. washwashed with 100 ml of acetonitrile
  6. customdried by air

Sources & evidence

ORD record
ord-6d00d166f67c4d8c97e2fdad420bb3ea
Source dataset
uspto-grants-1985_02
Patent number
US04500626

Reaction notes

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