Nitric Acid → N-(6-Chloro-5-nitro-1,3-benzothiazol-2-yl)-N'-ethylurea

HRID 9099Notes

Reaction equation

HRID 9099 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])[S:8][C:4]=2[CH:3]=1.[N+:17]([O-])([OH:19])=[O:18]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])[S:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 9964976N-(6-Chloro-1,3-benzothiazol-2-yl)-N'-ethylurea

Product 1

HCID 9922382N-(6-Chloro-5-nitro-1,3-benzothiazol-2-yl)-N'-ethylurea

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Three grams of N-(6-chloro-1,3-benzothiazol-2-yl)-N′-ethylurea was dissolved in about 15 mL of concentrated sulfuric acid (about 92–94%). The solution was cooled to about 0–5° C. About 1.5 g of ice cooled nitric acid (70% concentration was used, though this is not necessary) was added dropwise. The reaction was held at 0–5° C. for about one hour then poured into water. The pH was then adjusted to about 7–8 with ammonia and the solids were isolated by filtration. The solids were washed with water then dried in vacuo. The product was further purified by chromatography then dried in vacuo. 1H NMR 1.08 (t, 3H, J=7.2 Hz), 3.19 (m, 2H), 6.92 (br s, 1H), 8.26 (s, 1H), 8.31 (s, 1H), LC/MS 3.72 min, 302 (M+1)

Workup

  1. temperatureThe solution was cooled to about 0–5° C
  2. concentration70% concentration
  3. additionwas added dropwise
  4. additionthen poured into water
  5. customthe solids were isolated by filtration
  6. washThe solids were washed with water
  7. customthen dried in vacuo
  8. customThe product was further purified by chromatography
  9. customthen dried in vacuo
  10. custom1H NMR 1.08 (t, 3H, J=7.2 Hz), 3.19 (m, 2H), 6.92 (br s, 1H), 8.26 (s, 1H), 8.31 (s, 1H), LC/MS 3.72 min, 302 (M+1)

Sources & evidence

ORD record
ord-8fdf60b6ede54c5a9ab0db4f301291f1
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Reaction notes

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