Hydrochloric Acid → 8-Amino-3-cyanodibenzo[b,f]thiepin-5,5-dioxide

HRID 485442Notes

Reaction equation

HRID 485442 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH:12]=[CH:11][C:10]3[CH:13]=[C:14]([N+:17]([O-])=O)[CH:15]=[CH:16][C:9]=3[S:8](=[O:21])(=[O:20])[C:7]=2[CH:22]=1)#[N:2].Cl.[OH-].[Na+]>O1CCCC1>[NH2:17][C:14]1[CH:15]=[CH:16][C:9]2[S:8](=[O:21])(=[O:20])[C:7]3[CH:22]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=3[CH:12]=[CH:11][C:10]=2[CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 202702143-Cyano-8-nitrodibenzo[b,f]thiepin-5,5-dioxide

Product 1

HCID 131518848-Amino-3-cyanodibenzo[b,f]thiepin-5,5-dioxide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

875 Mg. 3-cyano-8-nitrodibenzo[b,f]thiepin-5,5-dioxide are dissolved in 105 cc. tetrahydrofuran. 15 CC. concentrated hydrochloric acid is added, followed by 3.8 g. stannous chloride dihydrate and the mixture is stirred for 24 hours. A solution of 20% sodium hydroxide is added, the mixture is shaken and the organic layer separated; the aqueous phase extracted once with ethyl acetate. The combined organic extracts are dried over sodium sulfate and evaporated to dryness. The residue is chromatographed on silica gel to yield 464 mg. (58%) pure amino compound, m.p. 321°-324° C.

Workup

  1. customthe organic layer separated
  2. extractionthe aqueous phase extracted once with ethyl acetate
  3. dry with materialThe combined organic extracts are dried over sodium sulfate
  4. customevaporated to dryness
  5. customThe residue is chromatographed on silica gel
  6. customto yield 464 mg

Sources & evidence

ORD record
ord-a80aefe9364e42cd9fef1462a23bff02
Source dataset
uspto-grants-1985_08
Patent number
US04536507

Reaction notes

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