Sulfuric Acid → 4-Acetamido-6-chloro-3,4-dihydro-spiro[2H-1-benzopyran-2,1'-cyclobutane]

HRID 1175760Notes

Reaction equation

HRID 1175760 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:13][C:9]3([CH2:12][CH2:11][CH2:10]3)[CH2:8][CH:7](O)[C:6]=2[CH:15]=1.S(=O)(=O)(O)[OH:17].[C:21](#[N:23])[CH3:22]>>[C:21]([NH:23][CH:7]1[C:6]2[CH:15]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:13][C:9]2([CH2:12][CH2:11][CH2:10]2)[CH2:8]1)(=[O:17])[CH3:22]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 6342Acetonitrile2×HCID 667463666-Chloro-3,4-dihydro-4-hydroxy-spiro[2H-1-benzopyran-2,1'-cyclobutane]

Product 1

HCID 667459764-Acetamido-6-chloro-3,4-dihydro-spiro[2H-1-benzopyran-2,1'-cyclobutane]

Procedure

A solution of 6-Chloro-3,4-dihydro-4-hydroxy-spiro[2H-1-benzopyran-2,1′-cyclobutane] (10 mmol) in acetonitrile (30-50 ml) was added to a solution of concentrated sulfuric acid (30 mmol) in acetonitrile (10 ml), at 0 to −10° C. The reaction mixture was stirred for about 2 hrs and was allowed to warm up, to room temperature. It was then added on ice. The corresponding acetamido derivative was separated out as a white solid which was filtered, washed with water and dried.

Workup

  1. additionIt was then added on ice
  2. customThe corresponding acetamido derivative was separated out as a white solid which
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-f4a814b853ac4c70bbd929350e34deb9
Source dataset
uspto-grants-2010_11
Patent number
US07842703B2

Reaction notes

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