Potassium cyanate → 5,6-dichloro-1,3-dihydro-1-(3-hydroxypropyl)-2H-benzimidazol-2-one

HRID 46851Notes

Reaction equation

HRID 46851 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[C:7]([Cl:9])[C:6]([Cl:10])=[CH:5][C:4]=1[NH:11][CH2:12][CH2:13][CH2:14][OH:15].[O-:16][C:17]#N.[K+]>O>[Cl:9][C:7]1[C:6]([Cl:10])=[CH:5][C:4]2[N:11]([CH2:12][CH2:13][CH2:14][OH:15])[C:17](=[O:16])[NH:2][C:3]=2[CH:8]=1

Participants

4

Reactant 2

HCID 11378442Potassium cyanateHCID 202880583-[(2-Amino-4,5-dichlorophenyl)amino]-1-propanol hydrochloride

Product 1

HCID 202880345,6-dichloro-1,3-dihydro-1-(3-hydroxypropyl)-2H-benzimidazol-2-oneYield 48%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred mixture of 31.2 parts of 3-[(2-amino-4,5-dichlorophenyl)amino]-1-propanol hydrochloride in 200 parts of water is added dropwise, during a 15 minutes-period, a solution of 10.6 parts of potassium cyanate in 50 parts of water at a temperature between 15° and 20° C. Upon completion, stirring is continued first for 20 minutes at room temperature and further for 20 hours at reflux. The reaction mixture is allowed to cool over week-end to room temperature. The precipitated product is filtered off and boiled in trichloromethane. The undissolved part is filtered off and boiled in 4-methyl-2-pentanone. After cooling, the product is filtered off and dried, yielding 14.5 parts (48%) of 5,6-dichloro-1,3-dihydro-1-(3-hydroxypropyl)-2H-benzimidazol-2-one; mp. 174.7° C.

Workup

  1. additionis added dropwise, during a 15 minutes-period
  2. customat a temperature between 15° and 20° C
  3. temperatureat reflux
  4. filtrationThe precipitated product is filtered off
  5. filtrationThe undissolved part is filtered off
  6. temperatureAfter cooling
  7. filtrationthe product is filtered off
  8. customdried

Sources & evidence

ORD record
ord-c55f803757df450995c25f82c2f09933
Source dataset
uspto-grants-1979_11
Patent number
US04175129

Reaction notes

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