Hydrochloric Acid → HCID 66636295, compound

HRID 44284

Reaction equation

HRID 44284 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[CH2:10][S:9][C:8]2=[O:20])=[CH:4][CH:3]=1.C([O:25][C:26](=O)[CH2:27][S:28][CH3:29])C.C(OCl)(C)(C)C.C(N(CC)CC)C.Cl.[OH-].[Na+]>CC#N.C1COCC1.C(Cl)Cl>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]2[CH2:10][S:9][C:8](=[O:20])[N:7]([CH2:6][C:5]3[CH:21]=[C:22]4[C:2](=[CH:3][CH:4]=3)[NH:1][C:26](=[O:25])[CH:27]4[S:28][CH3:29])[N:12]=2)=[CH:14][CH:15]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 78199Ethyl (methylthio)acetateHCID 521297Tert-Butyl hypochloriteHCID 666365703-(4-Amino-benzyl)-5-(4-chloro-phenyl)-3,6-dihydro-[1,3,4]thiadiazin-2-one

Product 1

HCID 66636295HCID 66636295, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

To a solution of the compound obtained in Step C (38.27 mmoles), in a mixture of CH3CN (115 ml) and THF (115 ml) at −60° C., ethyl(methylsulphanyl)acetate (45.92 mmoles) is added dropwise under a nitrogen atmosphere. tBuOCl (45.92 mmoles) is added dropwise to the reaction mixture over 20 minutes, keeping the temperature between −60° C. and −55° C. After stirring for 1 hour at −60° C., triethylamine (51.66 mmoles) is added dropwise. The reaction mixture is brought to ambient temperature. 240 ml of DCM and then aqueous 3M HCl solution (340 ml) are added. After stirring for 12 hours at ambient temperature, the reaction mixture is made alkaline (pH 10-11) using 20% aqueous sodium hydroxide solution. After extraction with DCM, the organic phase is washed with saturated aqueous NaCl solution. The organic phase is dried over sodium sulphate, filtered and evaporated to dryness. The product obtained is triturated in ethyl ether, filtered and dried in vacuo to yield the title product which is used directly in the next Step.

Workup

  1. customthe temperature between −60° C. and −55° C
  2. customis brought to ambient temperature
  3. stirringAfter stirring for 12 hours at ambient temperature
  4. extractionAfter extraction with DCM
  5. washthe organic phase is washed with saturated aqueous NaCl solution
  6. dry with materialThe organic phase is dried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe product obtained
  10. customis triturated in ethyl ether
  11. filtrationfiltered
  12. customdried in vacuo

Sources & evidence

ORD record
ord-721b27c7426a4fe0a4a241c1f831b5ac
Source dataset
uspto-grants-2013_09
Patent number
US08541412B2

Linked notes

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