Dicyclohexylcarbodiimide → 2-Amino-4-chlorobenzamide

HRID 481021노트

반응식

HRID 481021 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5](=[CH:9][CH:10]=1)[C:6](O)=[O:7].C1([N:18]=C=NC2CCCCC2)CCCCC1.O.OC1C2N=NNC=2C=CC=1.[OH-].[NH4+]>CN(C)C=O>[NH2:11][C:4]1[CH:3]=[C:2]([Cl:1])[CH:10]=[CH:9][C:5]=1[C:6]([NH2:18])=[O:7]

참가 물질

6

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 14923Ammonium HydroxideHCID 666462-Amino-4-chlorobenzoic acidHCID 178526939HCID 178526939, 화합물

생성물 1

HCID 123748372-Amino-4-chlorobenzamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-chloroanthranilic acid (70 g, 0.41 mol) in hot (60° C.) dimethylformamide (700 mL), dicyclohexylcarbodiimide (93 g, 0.451 mol, 1.1 equiv), hydroxybenzotriazole hydrate (60.9 g, 0.451 mol, 1.1 eq) and 30% aqueous ammonium hydroxide solution (350 mL) were added. The resulting solution was stirred at room temperature for 18 h. The formed urea was filtered off and the filtrate concentrated. The resulting mixture was partitioned between ethyl acetate and 5% K2CO3 solution. The organic phase was separated, dried over anhydrous Na2SO4, filtered and the filtrate was concentrated to dryness to give the desired product as a slightly yellow solid (58.1 g, 83%).

후처리

  1. filtrationThe formed urea was filtered off
  2. concentrationthe filtrate concentrated
  3. customThe resulting mixture was partitioned between ethyl acetate and 5% K2CO3 solution
  4. customThe organic phase was separated
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated to dryness

출처 및 근거

ORD 기록
ord-910b32b685cb4b8dab9eb0804869f0b6
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06653475B2

반응 노트

불러오는 중…