Ammonia → HCID 21487709, compound

HRID 1076587Notes

Reaction equation

HRID 1076587 reaction equation
[CH:1]1([CH2:4][N:5]2[C:10]3[S:11][CH:12]=[CH:13][C:9]=3[C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:7][C:6]2=[O:20])[CH2:3][CH2:2]1.C(OC(=O)C)(=O)C.[N+:28]([O-])([OH:30])=[O:29].N>>[CH:1]1([CH2:4][N:5]2[C:10]3[S:11][C:12]([N+:28]([O-:30])=[O:29])=[CH:13][C:9]=3[C:8]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[N:7][C:6]2=[O:20])[CH2:2][CH2:3]1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 944Nitric AcidHCID 7918Acetic Anhydride2×HCID 21487726HCID 21487726, compound

Product 1

HCID 21487709HCID 21487709, compound

Procedure

To a suspension of 380 mg of 1-cyclopropylmethyl-4-phenyl-1,2-dihydrothieno[2,3-d]pyrimidin-2-one and 1.2 ml of acetic anhydride is added 380 mg of fuming nitric acid (d = 1.50) is 1.20 ml of acetic anhydride. The reaction mixture is stirred for 48 hours at room temperature, then neutralized with aqueous ammonia under ice-cooling and extracted with chloroform. The chloroform extracts are washed with water, dried over sodium sulfate and evaporated under reduced pressure to give crystals, which are recrystallized from chloroform-ethanol to give 1-cyclopropylmethyl-4-phenyl-6-nitro-1,2-dihydrothieno[2,3-d]pyrimidin-2-one as crystals having a melting point of 216° - 218°C.

Workup

  1. temperaturecooling
  2. extractionextracted with chloroform
  3. washThe chloroform extracts are washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customto give crystals, which
  7. customare recrystallized from chloroform-ethanol

Sources & evidence

ORD record
ord-737da1bf54a2447ab55ca8b9a6a0af47
Source dataset
uspto-grants-1976_05
Patent number
US03957783

Reaction notes

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