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Sulfuric Acid → 1-(6-Chloro-2H-chromen-3-yl)-1H-imidazole

HRID 745975
Notes
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Reaction equation

HRID 745975 reaction equation
[N:1]1([CH:6]2[CH:11](O)[C:10]3[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:9]=3[O:8][CH2:7]2)[CH:5]=[CH:4][N:3]=[CH:2]1.S(=O)(=O)(O)O.[NH4+].[OH-]>C(O)(=O)C>[N:1]1([C:6]2[CH2:7][O:8][C:9]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:10]=3[CH:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 129536486-Chloro-3-(1H-imidazol-1-yl)-3,4-dihydro-2H-1-benzopyran-4-ol

Product 1

HCID 132878151-(6-Chloro-2H-chromen-3-yl)-1H-imidazoleYield 77.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes

A solution of 3-(1-imidazolyl)-2,3-dihydro-6-chloro-4H-1-benzopyran-4-ol (5.4 g), acetic acid (81 ml) and sulphuric acid (27 ml) was heated at 80° C. for 8 hours. The solution, poured into ice water (200 ml), neutralized with NH4OH, extracted with CH2Cl2, dried and evaporated to dryness gave 3.9 g of 3-(1-imidazolyl)-6-chloro-2H-1-benzopyran, m.p. 118°-120° C. (isopropyl alcohol).

Workup

  1. extractionextracted with CH2Cl2
  2. customdried
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-229b80a24b61461cb5adff4a4362e198
Source dataset
uspto-grants-1986_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04602022

Reaction notes

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