Dimethylamine → 1-(Dimethylamino)-3-(4-nitrophenoxy)propan-2-ol

HRID 1357550

反応式

HRID 1357550 の反応式
[O:1]1[CH2:14][CH:2]1[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.[CH3:15][NH:16][CH3:17]>CO.CN(C=O)C>[OH:1][CH:2]([CH2:14][N:16]([CH3:17])[CH3:15])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1

参加物

5

反応物 2

HCID 674DimethylamineHCID 213272-((4-Nitrophenoxy)methyl)oxirane

生成物 1

HCID 31320441-(Dimethylamino)-3-(4-nitrophenoxy)propan-2-ol

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 6228Dimethylformamide溶媒

実験手順

4-(2,3-Epoxypropoxy)nitrobenzene (obtained as described in Synthetic Communications, 1994, 24, 833; 4.3 g,) was dissolved in methanol (30 ml) and DMF (10 ml). A solution of dimethylamine in methanol (2M, 17 ml) was added and the mixture was stirred overnight. Volatile material was removed by evaporation and the residue was partitioned between saturated sodium bicarbonate (100 ml) and ethyl acetate (100 ml). The organic layer was separated and washed with saturated sodium chloride (2×100 ml) and dried. Concentration gave the product as an oil that slowly crystallised under high vacuum (4.79 g, 89.9%). NMR (CDCl3): 2.33 (s, 6H), 2.98 (m, 1H), 2.54 (m, 1H), 4.00 (m, 3H), 7.00 (d, 2H), 8.20 (d, 2H); MS (MH+): 241.

後処理

  1. customVolatile material was removed by evaporation
  2. customthe residue was partitioned between saturated sodium bicarbonate (100 ml) and ethyl acetate (100 ml)
  3. customThe organic layer was separated
  4. washwashed with saturated sodium chloride (2×100 ml)
  5. customdried
  6. concentrationConcentration

出典と根拠

ORDレコード
ord-f7e189f0aa2a44e496ed0a032d4e2d4b
出典データセット
uspto-grants-2003_07
特許番号
US06593326B1

関連ノート

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