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Hydrochloric Acid → (+/-)-cis-4-[[2-Amino-6-chloro-5-[(4-chlorophenyl)azo]-4-pyrimidinyl]amino]-2-cyclopentene-1-methanol

HRID 1534395
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HRID 1534395 반응식
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([NH:9][C@@H:10]2[CH2:14][C@H:13]([CH2:15][OH:16])[CH:12]=[CH:11]2)[N:3]=1.O.O.O.C([O-])(=O)C.[Na+].[Cl:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1.Cl.[N:34]([O-])=O.[Na+]>C(O)(=O)C.O>[Cl-:8].[Cl:25][C:26]1[CH:32]=[CH:31][C:29]([N+:30]#[N:1])=[CH:28][CH:27]=1.[NH2:1][C:2]1[N:3]=[C:4]([NH:9][C@@H:10]2[CH2:14][C@H:13]([CH2:15][OH:16])[CH:12]=[CH:11]2)[C:5]([N:34]=[N:30][C:29]2[CH:31]=[CH:32][C:26]([Cl:25])=[CH:27][CH:28]=2)=[C:6]([Cl:8])[N:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 78124-ChloroanilineHCID 11746763(+)-cis-4-[(2-Amino-4-chloro-6-pyrimidinyl)amino]-2-cyclopentene-1-methanolHCID 23665404Sodium Acetate TrihydrateHCID 23668193Sodium Nitrite

생성물 2

HCID 11819533Benzenediazonium, 4-chloro-, chloride
HCID 14503070
(+/-)-cis-4-[[2-Amino-6-chloro-5-[(4-chlorophenyl)azo]-4-pyrimidinyl]amino]-2-cyclopentene-1-methanol
수율 137.7%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

(±)-cis-4-[(2-Amino-4-chloro-6-pyrimidinyl)amino]-2-cyclopentene-1-methanol from Example 1 (11.58 g, 48.1 mmol) and sodium acetate trihydrate (97 g) were dissolved in glacial acetic acid (225 mL) and water (225 mL). A cold solution (0°-5° C.) of 4-chlorobenzenediazonium chloride was prepared from 4-chloroaniline (6.74 g, 52.8 mol), concentrated hydrochloric acid (14.7 mL) water (52 mL), and sodium nitrite (4.01 g, 58.2 mmol in 47 mL of water). This cold solution was added dropwise over 5 minutes to the first solution. The resulting yellow precipitate was filtered after 18 hours, washed with water, and extracted with ethanol to give title compound as dark yellow powder (12.56 g, 69%), m.p. 218°-220° C. dec.

후처리

  1. additionThis cold solution was added dropwise over 5 minutes to the first solution
  2. filtrationThe resulting yellow precipitate was filtered after 18 hours
  3. washwashed with water
  4. extractionextracted with ethanol

출처 및 근거

ORD 기록
ord-0cb9eb1b7ccf4b05a87a55ce2a44ae9e
출처 데이터셋
uspto-grants-1992_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05089500

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