Hydrochloric Acid → HCID 66937459, compound

HRID 408708Notes

Reaction equation

HRID 408708 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:17])[C:5]([NH2:16])=[CH:6][C:7]=1[S:8][C:9]1[CH:10]=[C:11]([CH3:15])[CH:12]=[CH:13][CH:14]=1.[CH:18](OC)(OC)OC.Cl>>[Cl:1][C:2]1[C:7]([S:8][C:9]2[CH:10]=[C:11]([CH3:15])[CH:12]=[CH:13][CH:14]=2)=[CH:6][C:5]2[N:16]=[CH:18][NH:17][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 9005Trimethyl orthoformateHCID 66937253HCID 66937253, compound

Product 1

HCID 66937459HCID 66937459, compound

Conditions

Temperature
23 °C

Procedure

To a cooled (0° C.) solution of 4-chloro-5-m-tolylsulfanyl-benzene-1,2-diamine (2.07 g, 7.80 mmol) and trimethyl orthoformate (5.81 mL, 53.0 mmol) was added concentrated HCl (0.722 mL, 11.5 mmol). The reaction mixture was warmed to 23° C. over 16 h, then concentrated under reduced pressure. EtOAc (100 mL) was added to the crude product and the organic layer was washed with saturated aqueous NaHCO3 (2×75 mL). The aqueous layer was extracted with EtOAc (2×50 mL). The organic layers were combined, dried, filtered, and concentrated under reduced pressure. The crude material was used in the next step without further purification. MS (ESI/CI): mass calcd. for C14H11ClN2S, 274.0; m/z found, 275.1 [M+H]+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionEtOAc (100 mL) was added to the crude product
  3. washthe organic layer was washed with saturated aqueous NaHCO3 (2×75 mL)
  4. extractionThe aqueous layer was extracted with EtOAc (2×50 mL)
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was used in the next step without further purification

Sources & evidence

ORD record
ord-18e17c0faa7d47b5a1914b0f975200db
Source dataset
uspto-grants-2014_06
Patent number
US08759345B2

Reaction notes

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