Phosphorus oxide (P4O10) → N,N,4-Trimethyl-4H-pyrrolo[2,1-c][1,4]benzoxazine-4-carboxamide

HRID 259039Notes

Reaction equation

HRID 259039 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1.[CH3:13][N:14]([CH3:20])[C:15](=[O:19])[C:16]([CH3:18])=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C1C=CC=CC=1>[CH3:13][N:14]([CH3:20])[C:15]([C:16]1([CH3:18])[C:9]2=[CH:10][CH:11]=[CH:12][N:8]2[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[O:1]1)=[O:19]

Participants

5

Reactant 3

HCID 14812Phosphorus oxide (P4O10)HCID 7123342-(1H-Pyrrol-1-Yl)PhenolHCID 13182523N,N-dimethyl-2-oxopropanamide

Product 1

HCID 12340637N,N,4-Trimethyl-4H-pyrrolo[2,1-c][1,4]benzoxazine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 1-(o-hydroxyphenyl)pyrrole (500 mg), N,N-dimethyl-pyruvamide (580 mg), described by W. F. Gresham in U.S. Pat. No. 2,429,877, issued Oct. 28, 1947, 1.7 g of phosphorus pentoxide, 0.5 g of diatomaceous earth (Celite) in 75 ml of benzene is stirred at room temperature for 15 min. and then at 70° C for 11/2 hr. The reaction mixture is filtered. The filtrate is washed with water, dried (MgSO4) and concentrated to give the title compound, identical to the product of Example 15.

Workup

  1. customat 70° C
  2. custom2 hr
  3. filtrationThe reaction mixture is filtered
  4. washThe filtrate is washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d4bfb27fd42b4f3dbc2e33cd42f29e3c
Source dataset
uspto-grants-1977_07
Patent number
US04035495

Reaction notes

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