Dichloromethane → Hydrochloric Acid

HRID 2292149Notes

Reaction equation

HRID 2292149 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[CH2:9][CH:10]([NH2:13])[CH2:11][S:12][C:7]=2[CH:6]=[CH:5][CH:4]=1.[C:14](OC(=O)C)(=O)[CH3:15].C(Cl)[Cl:22]>>[ClH:22].[ClH:22].[CH2:14]([NH:13][CH:10]1[CH2:9][C:8]2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[CH:6][C:7]=2[S:12][CH2:11]1)[CH3:15]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 143304585-Methoxy-3,4-dihydro-2H-1-benzothiopyran-3-amine

Product 2

HCID 313Hydrochloric AcidHCID 14330486HCID 14330486, compound

Procedure

A mixture of 500 mg of 3,4-dihydro-5-methoxy-2H-[1]-benzothiopyran-3-amine and 361 mg of acetic anhydride in 10 mL of methylene chloride is kept at room temperature for 15 min. The solvent is removed in vacuo and the resulting 3,4-dihydro-N-acetyl-5-methoxy-2H-[1]-benzopyran-3-amine is dissolved in 10 mL of 1M diborane in tetrahydrofuran. After 3 hr reflux, the reaction mixture is poured into 6N hydrochloric acid, washed with ether, basified with 45% potassium hydroxide and reextracted with ether. After drying over magnesium sulfate, the solvent is removed in vacuo. Acidification with ethanolic hydrochloric acid affords 3,4-dihydro-N-ethyl-5-methoxy-2H-[1]-benzothio-pyran-3-amine hydrochloride melting at 222°-224°.

Workup

  1. customThe solvent is removed in vacuo
  2. dissolutionthe resulting 3,4-dihydro-N-acetyl-5-methoxy-2H-[1]-benzopyran-3-amine is dissolved in 10 mL of 1M diborane in tetrahydrofuran
  3. temperatureAfter 3 hr reflux
  4. additionthe reaction mixture is poured into 6N hydrochloric acid
  5. washwashed with ether
  6. dry with materialAfter drying over magnesium sulfate
  7. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-23f7a3bab5cf4f2dbec9434a56641747
Source dataset
uspto-grants-1989_01
Patent number
US04801605

Reaction notes

Loading…