Cyanamide → HCID 178474228, compound

HRID 2400186Notes

Reaction equation

HRID 2400186 reaction equation
Cl.[C:2]([NH:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=1[NH2:15])(=[O:4])[CH3:3].[N:16]#[C:17][NH2:18]>O.Cl>[C:2]([NH:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=1[NH:15][C:17]([NH2:18])=[NH:16])(=[O:4])[CH3:3]

Participants

5

Reactant 2

HCID 9864CyanamideHCID 675678084-(Acetylamino)-3-Aminobenzoic Acid Hydrochloride

Product 1

HCID 178474228HCID 178474228, compoundYield 157.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolvent

Procedure

A mixture of 108 (100 mg, 0.43 mmol) and cyanamide (27 mg, 0.65 mmol) was mixed and heated at 85-100 C. with stirring for 15 minutes. The liquid mass was cooled to room temperature, dissolved in hot water (0.7 mL), and acidified with 1-2 drops of conc. HCl. The thick solid which separated was filtered and dried to give crude 113 (160 mg). This was recrystallized from 5% HCl to give the pure hydrochloride salt of 113 (50 mg, 52%): mp 284-287 C.

Workup

  1. additionwas mixed
  2. temperatureheated at 85-100 C
  3. customThe thick solid which separated
  4. filtrationwas filtered
  5. customdried

Sources & evidence

ORD record
ord-8a9f5e99436f4aeea7b95168c16017fb
Source dataset
uspto-grants-1995_09
Patent number
US05453533

Reaction notes

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