Methylamine → 3-Metoxycarbonyl-5-nitrobenzoyl-glycine methylamide

HRID 1606659

反応式

HRID 1606659 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:15]=[C:16]([N+:18]([O-:20])=[O:19])[CH:17]=1)[C:8]([NH:10][CH2:11][C:12]([OH:14])=O)=[O:9])=[O:4].C(Cl)(=O)O.[CH3:25][NH2:26]>O1CCCC1.C(N(CC)CC)C>[CH3:25][NH:26][C:12](=[O:14])[CH2:11][NH:10][C:8](=[O:9])[C:7]1[CH:15]=[C:16]([N+:18]([O-:20])=[O:19])[CH:17]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:6]=1

参加物

6

反応物 3

HCID 6329MethylamineHCID 164602Chloroformic acidHCID 21427264N-(3-Methoxycarbonyl-5-nitrobenzoyl)-glycine

生成物 1

HCID 214272733-Metoxycarbonyl-5-nitrobenzoyl-glycine methylamide

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8471Triethylamine溶媒

実験手順

Process 2: 8.5 g. (0.03 mole) of N-(3-metoxycarbonyl-5-nitrobenzoyl-glycine (VIa) dissolved in 130 ml. of absolute tetrahydrofuran, is cooled to -15° C., after the addition of 4.2 ml. of triethylamine, and mixed under agitation with 3 ml. of the ethyl ester of chlorocarbonic acid. The reaction mixture is agitated for about 10 minutes at -10° to -5° C., and a solution of 2.8 ml. of methylamine in 20 ml. of absolute tetrahydrofuran, cooled to -15° C., is gradually added thereto dropwise under agitation. Then, the mixture is stirred for another 30 minutes at -15° C. and subsequently overnight at room temperature; the triethylamine hydrochloride is filtered off, the filtrate concentrated under vacuum, and the residue recrystallized from acetonitrile; yield 4.6 g. m.p. 173°-174° C.

後処理

  1. additionafter the addition of 4.2 ml
  2. additionis gradually added
  3. stirringThen, the mixture is stirred for another 30 minutes at -15° C. and subsequently overnight at room temperature
  4. filtrationthe triethylamine hydrochloride is filtered off
  5. concentrationthe filtrate concentrated under vacuum
  6. customthe residue recrystallized from acetonitrile

出典と根拠

ORDレコード
ord-cff46c301bb1489bb5140c1444244d0c
出典データセット
uspto-grants-1976_04
特許番号
US03953501

関連ノート

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