Hydrogen Sulfide → HCID 86737453, compound

HRID 1389934Notes

Reaction equation

HRID 1389934 reaction equation
CO[C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8]C=2)[C:4]=1[CH:13]([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])[C:14]#[N:15].C(N(CC)CC)C.C[C:32](=[O:34])C.C(=O)=O.[SH2:38]>O.N1C=CC=CC=1>[CH3:32][O:34][CH:8]1[CH:7]=[CH:6][C:5]2[C:4](=[CH:3][CH:12]=[CH:11][CH:10]=2)[C:13]1([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])[C:14](=[S:38])[NH2:15]

Participants

7

Reactant 4

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 18522661Acetone cardiceHCID 20295994HCID 20295994, compound

Product 1

HCID 86737453HCID 86737453, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 12.1 parts of 2-methoxy-α-[(2-methylphenyl)amino]-1-naphthaleneacetonitrile, 4.1 parts of N,N-diethylethanamine and 20 parts of dry pyridine is stirred and cooled to 0° C. (cooling in a 2-propanone/CO2 -bath). During 2 hours, gaseous hydrogen sulfide is introduced. The whole is stored overnight at 0° C. The reaction mixture is poured onto 600 parts of water. The precipitated product is filtered off and dissolved in 450 parts of trichloromethane. The solution is washed with 100 parts of water, dried, filtered and evaporated. The residue is crystallized from 120 parts of acetonitrile. The product is filtered off (the filtrate is set aside) and dried, yielding a first fraction of 6.9 parts of 2-methoxy-α-[(2-methylphenyl)amino]-1-naphthalenecarbothioamide.

Workup

  1. waitThe whole is stored overnight at 0° C
  2. filtrationThe precipitated product is filtered off
  3. dissolutiondissolved in 450 parts of trichloromethane
  4. washThe solution is washed with 100 parts of water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is crystallized from 120 parts of acetonitrile
  9. filtrationThe product is filtered off (the filtrate
  10. customdried

Sources & evidence

ORD record
ord-2a71a01f65284a4ba17a8084eb22d1b3
Source dataset
uspto-grants-1981_01
Patent number
US04246429

Reaction notes

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