Benzyl mercaptan → HCID 20217508, compound

HRID 235808Notes

Reaction equation

HRID 235808 reaction equation
CC[O-].[Na+].[Na].[CH2:6]([SH:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[NH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[N:18][C:19](Cl)=[CH:20][CH:21]=2)[N:16]=1>O.C(O)C>[NH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[N:18][C:19]([S:13][CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[CH:20][CH:21]=2)[N:16]=1

Participants

7

Reactant 4

HCID 7509Benzyl mercaptanHCID 851997-Chloro-1,8-naphthyridin-2-amineHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 20217508HCID 20217508, compoundYield 57.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of sodium ethylate prepared from sodium (2.3 g) and ethanol (160 cc), benzyl mercaptan (13.6 g) is added and the mixture is stirred for 1 hour at a temperature in the region of 20° C. 2-Amino-7chloro-1,8-naphthyridine (18 g) is then added and the mixture is heated for 6 hours at 60° C. The suspension produced is poured into water (500 cc) and extracted with methylene chloride (3×250 cc). After being washed with water and dried, the organic solution is concentrated to dryness under reduced pressure (4 kPa) to give 2amino-7-benzylthio-1,8-naphthyridine (15.4 g), m.p. 167° C. EXAMPLE 11

Workup

  1. additionis added
  2. temperaturethe mixture is heated for 6 hours at 60° C
  3. customThe suspension produced
  4. extractionextracted with methylene chloride (3×250 cc)
  5. washAfter being washed with water
  6. customdried
  7. concentrationthe organic solution is concentrated to dryness under reduced pressure (4 kPa)

Sources & evidence

ORD record
ord-8b1fb6ceee294f4e89e60a98827f5cf0
Source dataset
uspto-grants-1987_02
Patent number
US04642308

Reaction notes

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