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

HRID 1534147
ノート
印刷プレビュー

反応式

HRID 1534147 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 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

生成物 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
収率 137.7%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

(±)-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 form 4-chloroaniline (6.74 g, 52.8 mmol), 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°-22° C. dec.

後処理

  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

出典と根拠

ORDレコード
ord-a7cb59d81df945cc91ae60ac85257718
出典データセット
uspto-grants-1992_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05087697

反応ノート

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