Triethylamine → N-[2-bromo-5-(3-dimethylaminobenzamido)phenyl]-3,4-dimethoxybenzamide

HRID 991419ノート

反応式

HRID 991419 の反応式
C(Cl)(=O)C(Cl)=O.[CH3:7][N:8]([CH3:18])[C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=O.[NH2:19][C:20]1[CH:21]=[CH:22][C:23]([Br:39])=[C:24]([NH:26][C:27](=[O:38])[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([O:36][CH3:37])[CH:29]=2)[CH:25]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C.CN(C)C1C=CN=CC=1>[Br:39][C:23]1[CH:22]=[CH:21][C:20]([NH:19][C:12](=[O:14])[C:11]2[CH:15]=[CH:16][CH:17]=[C:9]([N:8]([CH3:7])[CH3:18])[CH:10]=2)=[CH:25][C:24]=1[NH:26][C:27](=[O:38])[C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([O:36][CH3:37])[CH:29]=1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 668373-(Dimethylamino)benzoic acidHCID 18413858N-(5-amino-2-bromophenyl)-3,4-dimethoxybenzamide

生成物 1

HCID 9957535N-[2-bromo-5-(3-dimethylaminobenzamido)phenyl]-3,4-dimethoxybenzamide収率 56.8%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒3 回

反応条件

温度
7.5 °C

実験手順

Oxalyl chloride (0.24 ml) was added dropwise to a stirred suspension of 3-dimethylaminobenzoic acid (0.36 g) in methylene chloride (15 ml) at 20° C. DMF (2 drops) was added and the reaction mixture was stirred for 4 hours. The solvent was evaporated to give a yellow solid which was dissolved in methylene chloride (20 ml) and added dropwise over 5 minutes to a stirred mixture of N-(5-amino-2-bromophenyl)-3,4-dimethoxybenzamide (0.7 g), triethylamine (0.8 ml), 4-dimethylaminopyridine (0.005 g) and methylene chloride (20 ml) which had been cooled to 5-10° C. The reaction mixture was stirred at ambient temperature for 18 hours. The organic phase was washed with a saturated sodium bicarbonate solution, dried (MgSO4) and evaporated. The residual oil was purified by column chromatography on silica gel using a 49:1 mixture of methylene chloride and methanol as eluent. The solid so obtained was crystallised from a mixture of ethyl acetate and methyl tert-butyl ether to give the title compound (0.564 g), m.p. 184° C.;

後処理

  1. customThe solvent was evaporated
  2. customto give a yellow solid which
  3. stirringThe reaction mixture was stirred at ambient temperature for 18 hours
  4. washThe organic phase was washed with a saturated sodium bicarbonate solution
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residual oil was purified by column chromatography on silica gel using
  8. additiona 49:1 mixture of methylene chloride and methanol as eluent
  9. customThe solid so obtained
  10. customwas crystallised from a mixture of ethyl acetate and methyl tert-butyl ether

出典と根拠

ORDレコード
ord-5c1aeeec0c614b3ebb2b6cb028a19c3f
出典データセット
uspto-grants-2002_10
特許番号
US06465455B1

反応ノート

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