Hydrochloric Acid → 5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophen-4-amine hydrochloride

HRID 262048Notes

Reaction equation

HRID 262048 reaction equation
S1C=CC2C(=O)C=CC=CC1=2.[S:12]1[CH:16]=[CH:15][C:14]2[CH:17]([NH:22]C=O)[CH2:18][CH2:19][CH2:20][CH2:21][C:13]1=2.[ClH:25]>>[ClH:25].[S:12]1[CH:16]=[CH:15][C:14]2[CH:17]([NH2:22])[CH2:18][CH2:19][CH2:20][CH2:21][C:13]1=2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 123446374H-Cyclohepta[b]thiophen-4-oneHCID 21319849N-(5,6,7,8-tetrahydro-4H-cyclohepta[b]thien-4-yl)formamide

Product 1

HCID 213198545,6,7,8-tetrahydro-4H-cyclohepta[b]thiophen-4-amine hydrochloride

Procedure

5,6,7,8-Tetrahydro=4H-cyclohepta[b]thiophen-4-one is converted to N-(5,6,7,8-tetrahydro-4H-cyclohepta[b]thien-4-yl)formamide, m.p. 164°-166° C., by the method of Xloetzel et al., Journal of Organic Chemistry 18, 1511 (1953). Hydrolysis of the formanide is accomplished by refluxing for one hour in 1 N hydrochloric acid and evaporating to dryness to afford 5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophen-4-amine hydrochloride, m.p. 233°-236° C. dec. The amine hydrochloride is then allowed to react with methyl isocyanate in dry tetrahydrofuran as solvent in the presence of a stoichiometric equivalent of triethylamine to afford 1-methyl-3-(5,6,7,8-tetrahydro-4H-cyclohepta[b]thien-4-yl)urea, m.p. 220°-222° C.

Workup

  1. customHydrolysis of the formanide
  2. customevaporating to dryness

Sources & evidence

ORD record
ord-07b5db74bc4040b6bb8a9effec4feac7
Source dataset
uspto-grants-1979_05
Patent number
US04153611

Reaction notes

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