Hydrochloric Acid → HCID 70586825, compound

HRID 1732328Notes

Reaction equation

HRID 1732328 reaction equation
[Cl:1][C:2]1[C:12]([C:13](=[O:19])[C:14]2[S:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][C:5]2[CH2:6][CH:7]([CH:9]=O)[O:8][C:4]=2[C:3]=1[Cl:20].C([O-])(=O)C.[NH4+].C([BH3-])#[N:27].[Na+].Cl>CO>[NH2:27][C:7]1([CH3:9])[CH2:6][C:5]2[CH:11]=[C:12]([C:13](=[O:19])[C:14]3[S:18][CH:17]=[CH:16][CH:15]=3)[C:2]([Cl:1])=[C:3]([Cl:20])[C:4]=2[O:8]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 12747909HCID 12747909, compound

Product 1

HCID 70586825HCID 70586825, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A stirred solution containing 6,7-dichloro-2,3-dihydro-5-(2-thenoyl)benzofuran-2-carboxaldehyde (3.27 g., 0.01 mole) and ammonium acetate (6.16 g., 0.08 mole) in methanol (100 ml.) is treated with sodium cyanoborohydride (0.72 g., 0.0115 mole). After stirring 24 hours at 25° C., the reaction is acidified (pH below 2) with concentrated hydrochloric acid and the methanol is distilled at reduced pressure. The residue is stirred in water (25 ml.) for 15 minutes and then the mixture is extracted with ether (two 10 ml. portions). The aqueous layer is made basic (pH above 10) with potassium hydroxide pellets, saturated with sodium chloride and extracted with ether (two 10 ml. portions). The ether extract is dried over magnesium sulfate and the ether distilled under reduced pressure to give 2-amino-methyl-6,7-dichloro-2,3-dihydro-5-(2-thenoyl)benzofuran.

Workup

  1. distillationthe methanol is distilled at reduced pressure
  2. stirringThe residue is stirred in water (25 ml.) for 15 minutes
  3. extractionthe mixture is extracted with ether (two 10 ml. portions)
  4. extractionsaturated with sodium chloride and extracted with ether (two 10 ml. portions)
  5. extractionThe ether extract
  6. dry with materialis dried over magnesium sulfate
  7. distillationthe ether distilled under reduced pressure

Sources & evidence

ORD record
ord-13b568340947469fb0593c9a765b2bdc
Source dataset
uspto-grants-1980_12
Patent number
US04237144

Reaction notes

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