Benzoyl chloride → N-(3-Carboxymethyl-5-phenyl-2-thienyl)-benzamide

HRID 2082772

반응식

HRID 2082772 반응식
NC1SC(C2C=CC=CC=2)=CC=1C(OC)=O.C(CC(OC)=O)#N.C(Cl)(=O)C1C=CC=CC=1.[C:33]([CH2:36][C:37]1[CH:41]=[C:40]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[S:39][C:38]=1[NH:48][C:49]([CH:51]1[CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]1)=[O:50])([OH:35])=[O:34]>CN(C)P(N(C)C)(N(C)C)=O.O>[C:33]([CH2:36][C:37]1[CH:41]=[C:40]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[S:39][C:38]=1[NH:48][C:49](=[O:50])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)([OH:35])=[O:34]

참가 물질

7

반응물 4

HCID 7412Benzoyl chlorideHCID 7747Methyl cyanoacetateHCID 705256Methyl 2-amino-5-phenylthiophene-3-carboxylateHCID 23341632HCID 23341632, 화합물

생성물 1

HCID 23341625N-(3-Carboxymethyl-5-phenyl-2-thienyl)-benzamide

시약·촉매·용매 2

HCID 962Water용매HCID 12679Hexamethylphosphoramide용매

실험 절차

Methyl 2-amino-5-phenyl-thiophene-3-carboxylate (1.3 g, 0.0055 mole) in hexamethyl phosphoramide (prepared by the method of Chemische Berichte, 99, 94 (1966) but using methyl cyanoacetate in place of ethyl cyanoacetate) (20 ml.) was stirred and treated with benzoyl chloride (1.56 g, 1.28 ml, 0.011 mole). The solution was stirred for 2 hours, poured into water (750 ml), stored overnight and the title compound filtered off (1.31 g) m.p. 190° C. Similarly prepared was: N-(3-Carboxymethyl-5-phenyl-2-thienyl) cyclohexane carboxamide, m.p. 121°-122° C.

후처리

  1. stirringThe solution was stirred for 2 hours
  2. filtrationthe title compound filtered off (1.31 g) m.p. 190° C
  3. customSimilarly prepared

출처 및 근거

ORD 기록
ord-47bb0a7efc064b86a30d65c93c0fa913
출처 데이터셋
uspto-grants-1978_04
특허 번호
US04082771

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