Dicyclohexylcarbodiimide → HCID 178479381, compound

HRID 1073683Notes

Reaction equation

HRID 1073683 reaction equation
[ClH:1].[NH:2]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=1)[C:3]([NH2:5])=[NH:4].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[N+:40]([C:43]1[CH:52]=[CH:51][C:46]2[N:47]=[C:48]([NH2:50])[S:49][C:45]=2[CH:44]=1)([O-:42])=[O:41]>CN(C)C=O>[ClH:1].[NH:2]([C:6]1[CH:7]=[CH:8][C:9]([C:10]([NH:50][C:48]2[S:49][C:45]3[CH:44]=[C:43]([N+:40]([O-:42])=[O:41])[CH:52]=[CH:51][C:46]=3[N:47]=2)=[O:12])=[CH:13][CH:14]=1)[C:3]([NH2:5])=[NH:4]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 227042-Amino-6-nitrobenzothiazoleHCID 757711-HydroxybenzotriazoleHCID 178479383HCID 178479383, compound

Product 1

HCID 178479381HCID 178479381, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred, cold (-5° C.) solution of 1.07 g. of 4-guanidinobenzoic acid hydrochloride and 740 mg. of 1-hydroxybenzotriazole in 8 ml. of dimethylformamide was added 1.12 g. of dicyclohexylcarbodiimide in one portion. After two hours at 0° C., 950 mg. of 6-nitro-2-aminobenzothiazole was added and the reaction mixture was stirred at room temperature for two hours. The mixture was filtered and the filtrate applied to 35 g. of ionexchange resin GC 50 (H+ form). The column was washed with 200 ml. of water and sufficient methane until the washliquid became colorless. Following a second water/methanol wash the product was eluted from the column using a 0.05 M hydrochloric acid in methanol solution. The fractions containing the product are combined, concentrated to dryness and recrystallized from methanol, 60 mg., m.p. 311-329° C.

Workup

  1. customTo a stirred, cold (-5° C.) solution of 1.07 g
  2. filtrationThe mixture was filtered
  3. washThe column was washed with 200 ml
  4. washwash the product
  5. washwas eluted from the column
  6. additionThe fractions containing the product
  7. concentrationconcentrated to dryness
  8. customrecrystallized from methanol, 60 mg

Sources & evidence

ORD record
ord-23cc912917164fa8812fdc6af898ef67
Source dataset
uspto-grants-1990_11
Patent number
US04970318

Reaction notes

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