Carbon Dioxide → HCID 21496259, compound

HRID 1730750Notes

Reaction equation

HRID 1730750 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([S:16]([CH2:18][C:19]([OH:21])=[O:20])=[O:17])[CH3:15])=[CH:10][CH:9]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.C(=O)=O.[CH3:37][O:38][CH2:39][CH2:40]O>O1CCCC1>[CH3:37][O:38][CH2:39][CH2:40][O:20][C:19](=[O:21])[CH2:18][S:16]([CH:14]([C:11]1[CH:12]=[CH:13][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])=[CH:9][CH:10]=1)[CH3:15])=[O:17]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 80192-MethoxyethanolHCID 682631,1'-CarbonyldiimidazoleHCID 20348737HCID 20348737, compound

Product 1

HCID 21496259HCID 21496259, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 5.0 gm (16.4 millimols) of [1-(2'-fluoro-4-biphenylyl)-ethylsulfinyl]-acetic acid, m.p. 164° - 165° C, in 50 ml of dry tetrahydrofuran was admixed with 2.92 gm (18.1 millimols) of carbonyldiimidazole, whereupon the acid dissolved and carbon dioxide was given off. After one hour, 1.37 gm (18.1 millimols) of glycol monomethyl ether were added, and the mixture was allowed to stand for 2 hours. For isolation of the reaction product, the mixture was evaporated, and the residue was distributed between dilute hydrochloric acid and ethyl acetate, and the organic solution was purified by chromatography on 180 gm of silicagel with cyclohexane/ethyl acetate = 1/4. For further purification, the product mixture was recrystallized from cyclohexane/ethyl acetate = 4/1. Yield: 3.8 gm (63.8% of theory); m.p. 65°-67° C.

Workup

  1. dissolutiondissolved
  2. waitto stand for 2 hours
  3. customFor isolation of the reaction product, the mixture was evaporated
  4. customthe organic solution was purified by chromatography on 180 gm of silicagel with cyclohexane/ethyl acetate = 1/4
  5. customFor further purification
  6. customthe product mixture was recrystallized from cyclohexane/ethyl acetate = 4/1

Sources & evidence

ORD record
ord-a97b6bef47cb4e43b6fad0d8f2a3227d
Source dataset
uspto-grants-1976_11
Patent number
US03993683

Reaction notes

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