Hydrochloric Acid → HCID 12942114, compound

HRID 1577957Notes

Reaction equation

HRID 1577957 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:23][C:24](=[O:28])[N:25]([CH3:27])[CH3:26])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][C:12]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)OCC[O:13]1.O1CCCC1.Cl>[Cl-].[Na+].O>[C:12]([CH2:11][CH2:10][CH2:9][O:8][C:7]1[CH:6]=[CH:5][C:4]([NH:23][C:24](=[O:28])[N:25]([CH3:27])[CH3:26])=[CH:3][C:2]=1[Cl:1])(=[O:13])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 20566577HCID 20566577, compound

Product 1

HCID 12942114HCID 12942114, compound

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 3-{3-chloro-4-[3-(2-phenyl-1,3-dioxolan-2-yl)propoxy]phenyl}-1,1-dimethylurea (2.03 g; 0.005 mol), tetrahydrofuran (10 ml) and 10% aqueous hydrochloric acid (2 ml) is stirred overnight. The reaction mixture is poured into brine (100 ml) and extracted with methylene chloride. The organic layer is washed with water, dried and evaporated to afford the product: 1.69 g of an off-white solid. Recrystallization from a toluene-hexane mixture (50 ml) yields 1.33 g of cream colored needles, m.p. 129°-130° C.

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic layer is washed with water
  3. customdried
  4. customevaporated
  5. customto afford the product
  6. customRecrystallization from a toluene-hexane mixture (50 ml)
  7. customyields 1.33 g of cream colored needles, m.p. 129°-130° C.

Sources & evidence

ORD record
ord-4c369c9935624aebb4ccf274594aea31
Source dataset
uspto-grants-1981_09
Patent number
US04289903

Reaction notes

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