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

HRID 1591413Notes

Reaction equation

HRID 1591413 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 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.

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-08c253d0808644b9aef101c35cd02744
Source dataset
uspto-grants-1993_04
Patent number
US05206435

Reaction notes

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