Carbon Dioxide → HCID 18916423, compound

HRID 2395563Notes

Reaction equation

HRID 2395563 reaction equation
C([Li])CCC.[Cl:6][C:7]1[CH:12]=[CH:11][C:10](Cl)=[CH:9][C:8]=1[NH:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17].[C:21](=[O:23])=[O:22].[OH-].[Na+]>CCCCCC.O1CCCC1>[C:16]([C:15]1[O:20][C:9]2[C:10]([C:21]([OH:23])=[O:22])=[CH:11][CH:12]=[C:7]([Cl:6])[C:8]=2[N:14]=1)([CH3:19])([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 14798Sodium HydroxideHCID 4465103Propanamide, N-(2,5-dichlorophenyl)-2,2-dimethyl-HCID 178418339Butyllithium

Product 1

HCID 18916423HCID 18916423, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-20 °C

Procedure

n-Butyl lithium (101.6 ml of a 2.5M solution in hexane) was added during 30 minutes to a stirred solution of 2,5-dichloro-1-(trimethylacetylamino)benzene (25.0 g) in dry tetrahydrofuran at -40° C. and the solution stirred at -20° C. for 1.5 hours and poured onto solid carbon dioxide in dry tetrahydrofuran. The mixture was allowed to reach room temperature, 2M sodium hydroxide solution added and extracted with ethylacetate. The aqueous solution was acidified (concentrated hydrochloric acid) and the precipitated solid collected and dried to give 2-t-butyl-4-chlorobenzoxazole-7-carboxylic acid (1 1.7 g) m.p. 209°-210° C.

Workup

  1. customto reach room temperature
  2. extractionextracted with ethylacetate
  3. customthe precipitated solid collected
  4. customdried

Sources & evidence

ORD record
ord-dcfe97add816483f8e7107b64423865c
Source dataset
uspto-grants-1996_02
Patent number
US05489570

Reaction notes

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