Sodium Carbonate → N-carbobenzyloxy-4-(hexadecylamino)benzoyl chloride

HRID 2049091

反応式

HRID 2049091 の反応式
[CH2:1]([NH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(=O)([O-])[O-].[Na+].[Na+].[C:33](Cl)([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34].S(Cl)([Cl:46])=O>O.C(Cl)(Cl)Cl>[C:33]([N:17]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:18]1[CH:19]=[CH:20][C:21]([C:22]([Cl:46])=[O:24])=[CH:25][CH:26]=1)([O:35][CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:34]

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 24386Thionyl ChlorideHCID 472634-(Hexadecylamino)benzoic acid

生成物 1

HCID 20437379N-carbobenzyloxy-4-(hexadecylamino)benzoyl chloride

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6212Chloroform溶媒

反応条件

温度
40 °C

実験手順

To 15 g. (41.5 m moles) 4-(hexadecylamino)benzoic acid in 200 ml. warm chloroform is added 15 g. sodium carbonate in 150 ml. water. To the vigorously stirred solution is added 10 g. (59 m moles) carbobenzyloxy chloride. After 2 hours stirring at 40° C., the layers are separated, washed three times with 1 N hydrochloric acid, dried, and evaporated to an oil. The oil is dissolved in 300 ml. toluene, treated with 15 ml. (5 eq) thionyl chloride and the solution is refluxed for 5 hours. The solvents are evaporated and the residue is dissolved three times in toluene, evaporating each time to yield a viscous, orange oil.

後処理

  1. additionTo the vigorously stirred solution is added 10 g
  2. customthe layers are separated
  3. washwashed three times with 1 N hydrochloric acid
  4. customdried
  5. customevaporated to an oil
  6. dissolutionThe oil is dissolved in 300 ml
  7. additiontoluene, treated with 15 ml
  8. customThe solvents are evaporated
  9. dissolutionthe residue is dissolved three times in toluene
  10. customevaporating each time
  11. customto yield a viscous, orange oil

出典と根拠

ORDレコード
ord-719dcf0947bc4e5183450f61378b0a09
出典データセット
uspto-grants-1980_04
特許番号
US04196208

関連ノート

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