Sulfuric Acid → Ethyl (4-ChloroMethyl)couMarin-7-carbaMate

HRID 1901231Notes

Reaction equation

HRID 1901231 reaction equation
C([N:3]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])C.[Cl:16][CH2:17][C:18](=O)[CH2:19][C:20](OCC)=[O:21].OS(O)(=O)=O>>[C:4]([NH:3][C:9]1[CH:10]=[C:11]2[C:12]([C:18]([CH2:17][Cl:16])=[CH:19][C:20](=[O:21])[O:15]2)=[CH:13][CH:14]=1)([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 69484Ethyl 4-chloroacetoacetateHCID 22501398HCID 22501398, compound

Product 1

HCID 2434815Ethyl (4-ChloroMethyl)couMarin-7-carbaMateYield 86%

Procedure

A suspension of ethyl 3-hydroxyphenylurethane (1.81 g, 0.01 mole), ethyl 4-chloroacetoacetate (1.81 mL, 0.011 mole) and 70% H2SO4 (50 mL) is stirred for 4 hours at room temperature. The clear solution is poured into 400 mL of ice-water, with constant stirring, to yield a yellowish precipitate. The solid is filtered, washed with water and dried. The product is recrystallized from methanol to give colorless needles (86%).

Workup

  1. customto yield a yellowish precipitate
  2. filtrationThe solid is filtered
  3. washwashed with water
  4. customdried
  5. customThe product is recrystallized from methanol

Sources & evidence

ORD record
ord-8cdc643da8e74f51a9960da680ecf568
Source dataset
uspto-grants-1996_11
Patent number
US05576424

Reaction notes

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