Hydrochloric Acid → HCID 53913075, compound

HRID 1816761Notes

Reaction equation

HRID 1816761 reaction equation
C[O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:26][C@H:25]([CH3:27])[O:24][C@H:23]([CH3:28])[CH2:22]4)=[CH:17][CH:16]=3)=[N:13][N:14]=2)=[CH:6][CH:5]=1.[OH-].[Na+].CO.Cl>O.O1CCCC1>[CH3:28][C@H:23]1[O:24][C@@H:25]([CH3:27])[CH2:26][N:21]([C:18]2[CH:17]=[CH:16][C:15]([C:12]3[S:11][C:10]([C:7]4[CH:8]=[CH:9][C:4]([C:3]([OH:29])=[O:2])=[CH:5][CH:6]=4)=[N:14][N:13]=3)=[CH:20][CH:19]=2)[CH2:22]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 54358825HCID 54358825, compound

Product 1

HCID 53913075HCID 53913075, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-[5-[4-(cis-2,6-dimethylmorpholin-4-yl)phenyl][1,3,4]thiadiazol-2-yl]benzoic acid methyl ester (527 mg) and 1.0 mol/l sodium hydroxide solution (2.6 ml) in a mixed solvent of methanol (10 ml) and tetrahydrofuran (25 ml) was refluxed for 6 hours. After cooling to ambient temperature, the reaction mixture was poured into cold water and the mixture was adjusted with 1.0 mol/l hydrochloric acid. The resulting precipitates were filtered, washed with water and dried to give 4-[5-[4-(cis-2,6-dimethylmorpholin-4-yl)phenyl][1,3,4]thiadiazol-2-yl]benzoic acid (429.1 mg).

Workup

  1. temperaturewas refluxed for 6 hours
  2. customThe resulting precipitates
  3. filtrationwere filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-7e2e72fc6cad479b81143d1bc8be7f4e
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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