Sulfuric Acid → HCID 20296014, compound

HRID 1389932Notes

Reaction equation

HRID 1389932 reaction equation
S(=O)(=O)(O)[OH:2].[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:8]=1[CH:14]([NH:17][C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=1)[C:15]#[N:16]>>[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:8]=1[CH:14]([NH:17][C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=1)[C:15]([NH2:16])=[O:2]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 20295988HCID 20295988, compound

Product 1

HCID 20296014HCID 20296014, compound

Procedure

To 360 parts of concentrated sulfuric acid are added portionwise 30 parts of 2,6-dichloro-α-[(2-naphthalenyl)amino]benzeneacetonitrile and the whole is stirred till all solid enters solution. The reaction solution is allowed to stand overnight at room temperature and then poured onto 1000 parts of crushed ice. The precipitated product is filtered off and extracted with 1500 parts of chloroform. The organic phase is washed with water, dried, filtered and evaporated. The oily residue solidifies on triturating in 2-propanol. The solid product is filtered off and crystallized from 200 parts of 2-propanol at 0° C., yielding 11.3 parts of 2,6-dichloro-α-[(2-naphthalenyl)amino]benzeneacetamide; mp. 157.9° C.

Workup

  1. additionpoured onto 1000 parts of crushed ice
  2. filtrationThe precipitated product is filtered off
  3. extractionextracted with 1500 parts of chloroform
  4. washThe organic phase is washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customon triturating in 2-propanol
  9. filtrationThe solid product is filtered off
  10. customcrystallized from 200 parts of 2-propanol at 0° C.

Sources & evidence

ORD record
ord-bd2c1103d14f4923b5843654b7fa0d1d
Source dataset
uspto-grants-1981_01
Patent number
US04246429

Reaction notes

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