Chloroacetyl chloride → Ethyl 2-(chloromethyl)-1,3-benzoxazole-5-carboxylate

HRID 465046노트

반응식

HRID 465046 반응식
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[N+:13]([O-])=O.[Cl:16][CH2:17][C:18](Cl)=O.P(Cl)(Cl)(Cl)=O>[Ni].C(O)C>[Cl:16][CH2:17][C:18]1[O:1][C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=2[N:13]=1

참가 물질

6

반응물 3

HCID 6577Chloroacetyl chlorideHCID 24813Phosphorus oxychlorideHCID 87895Benzoic acid, 4-hydroxy-3-nitro-, ethyl ester

생성물 1

HCID 15211498Ethyl 2-(chloromethyl)-1,3-benzoxazole-5-carboxylate

시약·촉매·용매 2

HCID 935Nickel촉매HCID 702Ethanol용매

실험 절차

Ethyl 4-hydroxy-3-nitrobenzoate (32 g) prepared according to the method described in J. Org. Chem., vol. 26, p. 2223 (1961) was subjected to reduction under increased pressure at 70 atm in the presence of a Raney Nickel catalyst in absolute ethanol (200 ml). The product was then caused to react with chloroacetyl chloride, and was subsequently subjected to ring closure with phosphorous oxychloride to yield 2-chloromethyl-5-ethoxycarbonylbenzoxazole (27.3 g). The chloromethyl compound (10 g) was caused to react with dimethylamine to yield 2-dimethylaminomethyl-5-ethoxycarbonylbenzoxazole (6 g), which was subsequently subjected to reduction with lithium aluminium hydride in anhydrous tetrahydrofuran (60 ml) thereby to obtain 2-dimethylaminomethyl-5-hydroxymethylbenzoxazole (2 g).

출처 및 근거

ORD 기록
ord-f637b528364845b0bd11923a64889953
출처 데이터셋
uspto-grants-1985_10
특허 번호
US04550118

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