Phosphorus oxychloride → HCID 21104381, compound

HRID 1354100Notes

Reaction equation

HRID 1354100 reaction equation
[CH3:1][C:2]1[NH:11][C:10](=O)[C:9]2[CH2:8][CH2:7][CH2:6][C:5]([CH2:16][CH2:17][CH3:18])([CH2:13][CH2:14][CH3:15])[C:4]=2[N:3]=1.O=P(Cl)(Cl)[Cl:21]>>[Cl:21][C:10]1[C:9]2[CH2:8][CH2:7][CH2:6][C:5]([CH2:16][CH2:17][CH3:18])([CH2:13][CH2:14][CH3:15])[C:4]=2[N:3]=[C:2]([CH3:1])[N:11]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136008009HCID 136008009, compound

Product 1

HCID 21104381HCID 21104381, compoundYield 87%

Procedure

2-Methyl-8,8-dipropyl-5,6,7,8-tetrahydro-3H-quinazolin-4-one (180 mg, 0.72 mmol) and POCl3 (3 mL) were combined and heated under reflux for 6 hrs. The excess POCl3 was evaporated under reduced pressure. The residue was taken up in CH2Cl2 (25 mL), washed with cold water, sat. NaHCO3 solution., brine and dried over MgSO4. The CH2Cl2 solution was passed through a short (22 mm×20 cm) SiO2 column, eluting with CH2Cl2. Evaporation afforded 169 mg (87%) of 4-chloro-2-methyl-8,8-dipropyl-5,6,7,8-tetrahydroquinazoline as a pale yellow viscous liquid. MS (ES+) 267 (M+H).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 6 hrs
  3. customThe excess POCl3 was evaporated under reduced pressure
  4. washwashed with cold water, sat. NaHCO3 solution
  5. dry with material, brine and dried over MgSO4
  6. washeluting with CH2Cl2
  7. customEvaporation

Sources & evidence

ORD record
ord-b7e2ef5fd8664b28988eadedba7e256a
Source dataset
uspto-grants-2007_05
Patent number
US07223767B2

Reaction notes

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