Hydrochloric Acid → HCID 178498868, compound

HRID 621388Notes

Reaction equation

HRID 621388 reaction equation
[CH3:1][CH:2](C(O)=O)[N:3]([CH:6]1[CH:15]2[CH:10]([CH2:11][CH2:12][CH2:13][CH2:14]2)[CH2:9][CH2:8][CH2:7]1)C=O.[CH:19]([O:21][CH3:22])=[O:20].[H-].[Na+].Cl.[S-:26][C:27]#[N:28].[K+]>O.CO.O(CC)CC.O1CCCC1>[SH:26][C:27]1[N:3]([CH:6]2[CH:15]3[CH:10]([CH2:11][CH2:12][CH2:13][CH2:14]3)[CH2:9][CH2:8][CH2:7]2)[C:2]([C:19]([O:21][CH3:22])=[O:20])=[CH:1][N:28]=1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 7865Methyl formateHCID 24758Sodium hydrideHCID 516872Potassium thiocyanateHCID 86742951methyl N-(decahydro-1-naphthalenyl)-N-formylglycine

Product 1

HCID 178498868HCID 178498868, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl N-(decahydro-1-naphthalenyl)-N-formylglycine in 900 parts of tetrahydrofuran and 127 parts of methyl formate were added suitable amounts of sodium hydride. After stirring for 18 hours at room temperature, 350 parts of deionisized water and 1.4 parts of 1,1'-oxybisethane were added to the mixture. The separated aqueous layer was acidified with 132.7 parts of concentrated hydrochloric acid and 280 parts of methanol were added. The whole was heated to 40°-50° C. and treated with a solution of 92.7 parts of potassium thiocyanate in 200 parts of deionisized water. The whole was stirred for 22 hours at room temperature. The precipitated product was filtered off and crystallized from methanol. The product was filtered off and dried, yielding methyl 2-mercapto-N-(decahydro-1-naphthalenyl)-1H-imidazole-5-carboxylate; mp. 179°-181° C. (compound 1.15).

Workup

  1. additionwere added
  2. temperatureThe whole was heated to 40°-50° C.
  3. stirringThe whole was stirred for 22 hours at room temperature
  4. filtrationThe precipitated product was filtered off
  5. customcrystallized from methanol
  6. filtrationThe product was filtered off
  7. customdried

Sources & evidence

ORD record
ord-80785f56f320434fb5b0c1e003a5c17d
Source dataset
uspto-grants-1989_04
Patent number
US04824472

Reaction notes

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