Ammonia → 10-(3-Chloropropyl)-10H-phenoxazine

HRID 1491587Notes

Reaction equation

HRID 1491587 reaction equation
[NH2-].[Na+].N.[CH:4]1[C:17]2[NH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[O:9][C:8]=2[CH:7]=[CH:6][CH:5]=1.Br[CH2:19][CH2:20][CH2:21][Cl:22]>>[Cl:22][CH2:21][CH2:20][CH2:19][N:16]1[C:17]2[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=2[O:9][C:10]2[C:15]1=[CH:14][CH:13]=[CH:12][CH:11]=2

Participants

5

Reactant 4

HCID 222Ammonia2×HCID 80061-Bromo-3-chloropropaneHCID 24533Sodium amideHCID 67278Phenoxazine

Product 1

HCID 1008392610-(3-Chloropropyl)-10H-phenoxazine

Procedure

To a suspension of sodium amide (1.72 g) in 100 ml of liquid ammonia, 7 g (0.038 mol) of phenoxazine was added. After stirring for 30 minutes, 6.3 g (0.04 mol., 3.96 mL) of 1-bromo-3-chloropropane was added slowly with constant stirring. After one more hour, ammonia was allowed to evaporate and solid ice pieces were added carefully followed by cold water. When the reaction ceased, the mixture was extracted three times with ether. The ether solution was washed three times with water, dried over anhydrous sodium sulfate and evaporated. The residue was chromatographed on silica gel. Petroleum ether-ethylacetate (9 mL+3 mL) eluted the pure title compound (7.94 g) as white crystals. VU-λmax (MeOH) 218, 238 and 321 nm; IR (KBr) 3070, 2860, 1630, 1490, 1380, 1275, 920, 815 and 740 cm-1 ; 1H-NMR (δ) 6.47-6.82 (m, 8H, ArH, H1 -H4 and H6 -H9), 2.11 (m, 2H, H1), 3.63 (m, 2H, HK), and 3.69 (m, 2H, Hm); 13C-NMR (1H decoupled) 111.23 (C1 and C9), 115.50 (C4 and C6), 121.07 (C3 and C7), 123.70 (C2 and C8), 133.03 (C1' and C9'), 144.92 (C4' and C6'), 27.82 (C1), 41.09 (CK) and 42.63 (Cm); EIMS (m/z) 259 (M+).

Workup

  1. additionwas added
  2. customto evaporate
  3. additionsolid ice pieces were added carefully
  4. extractionthe mixture was extracted three times with ether
  5. washThe ether solution was washed three times with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated
  8. customThe residue was chromatographed on silica gel
  9. washPetroleum ether-ethylacetate (9 mL+3 mL) eluted the pure title compound (7.94 g) as white crystals

Sources & evidence

ORD record
ord-42cba10020224fabb01ed3a62bde5106
Source dataset
uspto-grants-1994_12
Patent number
US05371081

Reaction notes

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