Hydrochloric Acid → HCID 178422984, compound

HRID 501787Notes

Reaction equation

HRID 501787 reaction equation
O[NH:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[OH:11].C(N(CC)CC)C.S(Cl)(Cl)=O.Cl>O1CCCC1.O>[CH3:10][C:7]1[CH:8]=[CH:9][C:4]2[C:3]([OH:12])=[N:2][O:11][C:5]=2[CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 23021540N,2-dihydroxy-4-methylbenzamide

Product 1

HCID 178422984HCID 178422984, compoundYield 89.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

44.0 g of N,2-dihydroxy-4-methylbenzamide was suspended in 880 mL of tetrahydrofuran, to which 147 mL of triethylamine was added dropwise at room temperature and then 28.7 mL of thionyl chloride was added dropwise at 5 to 10° C. successively, and this mixture was stirred for one hour at room temperature. The reaction mixture was added to water, and adjusted to pH 1 with 12M hydrochloric acid, and then resultant precipitate was filtered out thereof. The resultant solid was washed with water to yield 35.2 g of 6-methyl-1,2-benzisoxazol-3-ol as light yellow solid.

Workup

  1. additionwas added dropwise at room temperature
  2. filtrationresultant precipitate was filtered out thereof
  3. washThe resultant solid was washed with water

Sources & evidence

ORD record
ord-0dbf453ba57d4c57bee8b19a1d6b81b0
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

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