Thionyl Chloride → Ska-31

HRID 1382708

Reaction equation

HRID 1382708 reaction equation
S(Cl)(Cl)=O.[C:5]1([NH:15][C:16]([NH2:18])=[S:17])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1>C(OCC)(=O)C>[N:15]1[C:5]2[C:14]3[C:9]([CH:8]=[CH:7][C:6]=2[S:17][C:16]=1[NH2:18])=[CH:10][CH:11]=[CH:12][CH:13]=3

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 736366Alpha-Naphthylthiourea

Product 1

HCID 94880Ska-31Yield 74%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 160 ml thionyl chloride 64.0 g (0.32 mol) of 1-(1-naphthyl)-2-thiourea was added portionwise while the temperature of the reaction mixture was kept at 30°-40° (internal temperature). After the addition was completed, an additional 80 ml of thionyl chloride was added and the mixture was heated at 50°-55° for 4 hours. It was cooled to room temperature and diluted with 400 ml of ethyl acetate and filtered. The filtrate in 400 ml of water was basified with concentrated ammonium hydroxide and the aqueous suspension was extracted with ethyl acetate (3×200 ml). The combined ethyl acetate solutions were dried (MgSO4) and the solvent was removed under reduced pressure to give 46.6 g (74%) of naphtho[1,2-d]thiazol-2-amine, mp 186°-188°.

Workup

  1. customwas kept at 30°-40°
  2. additionAfter the addition
  3. temperaturethe mixture was heated at 50°-55° for 4 hours
  4. filtrationfiltered
  5. extractionthe aqueous suspension was extracted with ethyl acetate (3×200 ml)
  6. dry with materialThe combined ethyl acetate solutions were dried (MgSO4)
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6a8cb38c03b64bcd85de0f54e3e82f3c
Source dataset
uspto-grants-1989_02
Patent number
US04808580

Linked notes

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