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

HRID 1534147Notes

Reaction equation

HRID 1534147 reaction equation
[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

Participants

9

Reactant 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

Product 2

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

(±)-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.

Workup

  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

Sources & evidence

ORD record
ord-a7cb59d81df945cc91ae60ac85257718
Source dataset
uspto-grants-1992_02
Patent number
US05087697

Reaction notes

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