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Bromomethyl 4-methoxyphenyl ketone → 4-[4-Amino-5-(4-methoxy-benzoyl)-thiazol-2-ylamino]-benzoic Acid Methyl Ester

HRID 413731
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HRID 413731 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]=[C:12]=[S:13])=[CH:7][CH:6]=1)=[O:4].[N:14]#[C:15][NH2:16].CC(C)([O-])C.[K+].Br[CH2:24][C:25]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)=[O:26]>C(#N)C.C(O)(C)(C)C.O>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[S:13][C:24]([C:25](=[O:26])[C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)=[C:15]([NH2:16])[N:14]=2)=[CH:7][CH:6]=1
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참가 물질

8

반응물 4

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 9864CyanamideHCID 1380024-Methoxycarbonylphenyl isothiocyanateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 205905724-[4-Amino-5-(4-methoxy-benzoyl)-thiazol-2-ylamino]-benzoic Acid Methyl Ester수율 90%

시약·촉매·용매 3

HCID 962
Water
용매
HCID 6342Acetonitrile용매
HCID 6386tert-Butanol용매

실험 절차

To a mixture of 4-methoxycarbonylphenyl isothiocyanate (82 mg, 0.5 mmol) and cyanamide (23 mg, 0.55 mmol) in acetonitrile (5 mL), a solution of potassium tert-butoxide (61 mg, 0.55 mmol) in tert-butanol (5 mL) was added. After 30 minutes at ambient temperature, 2-bromo-4′-methoxy-acetophenone (115 mg, 0.5 mmol) was added. After 2 hours at ambient temperature, the reaction mixture was diluted with water (50 mL). The product was collected by filtration, rinsed with water and ethyl ether, and dried under vacuum to furnish a yellow solid, 172 mg (90% yield).

후처리

  1. waitAfter 2 hours at ambient temperature
  2. filtrationThe product was collected by filtration
  3. washrinsed with water and ethyl ether
  4. customdried under vacuum
  5. customto furnish a yellow solid, 172 mg (90% yield)

출처 및 근거

ORD 기록
ord-6593ffcf737147e6a98eae6e86443688
출처 데이터셋
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06569878B1

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