Hydrochloric Acid → HCID 12096470, compound

HRID 2120091Notes

Reaction equation

HRID 2120091 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])(=[O:3])[CH3:2].[CH3:11][N:12]=[C:13]=[S:14].NC(N)=S.[CH3:19][C:20]1[C:21](=[O:31])[C:22]2[C:27]([C:28](=O)[CH:29]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2.[ClH:32]>C(O)C>[Cl-:32].[C:1]([C:4]1[CH:5]=[C:6]([NH:7][C:13]2[S:14][C:29]3[C:20]([CH3:19])=[C:21]([OH:31])[C:22]4[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:28]=3[N+:12]=2[CH3:11])[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 4055MenadioneHCID 74173'-AminoacetophenoneHCID 11167Methyl isothiocyanateHCID 2723790Thiourea

Product 1

HCID 12096470HCID 12096470, compoundYield 24.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

3-acetylaniline (6.76 g, 50 mmole) in ethanol (50 mL) was treated with methyl isothiocyanate (3.42 mL, 50 mmole). After stirring 18 hr at room temperature, the crystalline N-(3-acetylphenyl)-N′-methylthiourea product was filtered out (7.75 g, 75% yield, mp 119-120° C.). This thiourea (3.5 g, 16.8 mmole) was combined with 2-methylnaphthoquinone (5.8 g, 33.6 mmole) in 35 mL ethanol in the presence of 12N aq. HCl (1.4 mL, 16.8 mmole). After 24 hr, filtration and washing with ethanol, ethyl acetate and ether and air drying gave 2-(3-acetylphenyl)amino-1,4-dimethyl-5-hydroxynaphtho[1,2-d]thiazolium chloride (1.62 g, 24%). This keto naphthothiazolium salt (0.80 g, 2.0 mmole) was heated at reflux in 80% methanol (12 mL) containing aminoguanidine hydrochloride (0.24 g, 2.2 mmole) for 40 hr and allowed to cool. Filtration 0.80 g off-white powder. Recrystallization of 0.75 g from methanol gave 0.42 g 2-[[3-[1-[2-(aminoiminomethyl)hydrazono]ethyl]phenyl]amino]-4-methylnaphtho[1,2-d]thiazol-5-ol as a pale yellow powder, mp 252-257° C. (dec.).

Workup

  1. filtrationthe crystalline N-(3-acetylphenyl)-N′-methylthiourea product was filtered out (7.75 g, 75% yield, mp 119-120° C.)
  2. waitAfter 24 hr
  3. filtrationfiltration
  4. washwashing with ethanol, ethyl acetate and ether and air
  5. customdrying

Sources & evidence

ORD record
ord-ec58e9b32ea54a92848202d99c602293
Source dataset
uspto-grants-2004_02
Patent number
US06689777B2

Reaction notes

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