2,5-Dimethoxytetrahydrofuran → N-(7-Nitro-2,4-dioxo-6-pyrrol-1-yl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide

HRID 2069198Notes

Reaction equation

HRID 2069198 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[NH:8][C:7](=[O:15])[N:6]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[C:5]2=[O:21].CO[CH:24]1[CH2:28][CH2:27][CH:26](OC)O1>C(O)(=O)C.C(OCC)C>[N+:12]([C:11]1[CH:10]=[C:9]2[C:4]([C:5](=[O:21])[N:6]([NH:16][S:17]([CH3:20])(=[O:18])=[O:19])[C:7](=[O:15])[NH:8]2)=[CH:3][C:2]=1[N:1]1[CH:24]=[CH:28][CH:27]=[CH:26]1)([O-:14])=[O:13]

Participants

5

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 11674068N-(6-Amino-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide

Product 1

HCID 11545096N-(7-Nitro-2,4-dioxo-6-pyrrol-1-yl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of N-(6-amino-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide (90 mg, 0.285 mmol) and 2,5-dimethoxytetrahydrofuran (0.038 ml, 0.291 mmol) in acetic acid (0.5 ml) is refluxed for 80 minutes. The resulting suspension is filtered and the residue washed with ethyl acetate. The filtrate is concentrated in vacuo to give a brown solid which is suspended in diethyl ether and filtered to give a brown-orange solid as the desired pure product, m.p. 243-250° C.

Workup

  1. filtrationThe resulting suspension is filtered
  2. washthe residue washed with ethyl acetate
  3. concentrationThe filtrate is concentrated in vacuo
  4. customto give a brown solid which
  5. filtrationfiltered
  6. customto give a brown-orange solid as the desired pure product, m.p. 243-250° C.

Sources & evidence

ORD record
ord-57ac8f659f1e43e39a946cea55f4d616
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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