Methanol → Hydrochloric Acid

HRID 1948630Notes

Reaction equation

HRID 1948630 reaction equation
CO.C([Cl:6])(=O)C.C(=O)([S:9][CH2:10][CH2:11][C:12]1[C:20]2[C:15](=[N:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)C>CO.ClCCl>[ClH:6].[NH:14]1[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:20]2[C:12]([CH2:11][CH2:10][SH:9])=[CH:13]1.[ClH:6]

Participants

6

Reactant 3

HCID 887MethanolHCID 6367Acetyl chlorideHCID 91204743HCID 91204743, compound

Product 2

HCID 313Hydrochloric AcidYield 582%HCID 87642510HCID 87642510, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Methanol (20 ml) was cooled to below 0° C. under argon. Acetyl chloride (3 ml, 42 mmole) was then slowly added dropwise. The reaction was exothermic. The temperature was maintained below 15° C. during the dropwise addition. The reaction mixture was stirred for 1 hour at room temperature. S-2-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethyl ethanethioate (600 mg, 2.724 mmole) was dissolved in methanol/dichloromethane 1:1 (10 ml) and then added dropwise within 10 minutes. The reaction mixture was stirred for 18 hours at 23° C. The solvent was distilled off. The orange residue was suspended in cyclohexane (5 ml), filtered and washed with cyclohexane (3×1 ml). The beige-coloured Ind-4 was presumably obtained as hydrochloride (578 mg, 99%, melting point 138-150° C.).

Workup

  1. temperatureThe temperature was maintained below 15° C. during the dropwise addition
  2. additionadded dropwise within 10 minutes
  3. stirringThe reaction mixture was stirred for 18 hours at 23° C
  4. distillationThe solvent was distilled off
  5. filtrationfiltered
  6. washwashed with cyclohexane (3×1 ml)

Sources & evidence

ORD record
ord-dec3b56af0094c9281103e2bd77749da
Source dataset
uspto-grants-2013_03
Patent number
US08399503B2

Reaction notes

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