4-Nitrophenol → HCID 178521452, compound

HRID 847229Notes

Reaction equation

HRID 847229 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][C@@H:14]2[CH2:19][CH2:18][C@H:17](CC(O)=O)[CH2:16][CH2:15]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(C1NC=CN=1)(C1NC=CN=1)=[O:25].[N+](C1C=[CH:43][C:42]([OH:45])=CC=1)([O-])=O.[NH2:46][C:47]1[NH:51][N:50]=[N:49][N:48]=1>O1CCCC1>[NH:48]1[C:47]([NH:46][C:42](=[O:45])[CH2:43][O:25][C@H:17]2[CH2:16][CH2:15][C@@H:14]([CH2:13][CH2:12][NH:11][S:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)(=[O:9])=[O:10])[CH2:19][CH2:18]2)=[N:51][N:50]=[N:49]1

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 178509299HCID 178509299, compoundHCID 178525565HCID 178525565, compound

Product 1

HCID 178521452HCID 178521452, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.0 g. (5.3 mMol) cis-4-[2-(4-chlorobenzenesulphonylamino)-ethyl]-cyclohexylacetic acid and 25 ml. anhydrous tetrahydrofuran is added drop-wise 0.86 g. (5.3 mMol) carbonyl-bis-imidazole. The reaction mixture is stirred for 10 minutes, 0.74 g. (5.3 mMol) 4-nitrophenol is added thereto, followed by further stirring for 10 minutes at 40° C. 0.91 g. (100 mMol) anhydrous 5-amino-1,2,3,4-tetrazole is then added thereto. The reaction mixture is kept at 60° C. for 3 hours, then evaporated in a vacuum and the residue is stirred with 0.5N hydrochloric acid. After filtering off with suction and washing with water, the product obtained is recrystallised from ethanol. Yield 1.40 g. (59% of theory); m.p. 191°-192° C.

Workup

  1. stirringby further stirring for 10 minutes at 40° C
  2. waitThe reaction mixture is kept at 60° C. for 3 hours
  3. customevaporated in a vacuum
  4. stirringthe residue is stirred with 0.5N hydrochloric acid
  5. filtrationAfter filtering off with suction
  6. washwashing with water
  7. customthe product obtained
  8. customis recrystallised from ethanol

Sources & evidence

ORD record
ord-ef1fbbcaa03e4a74a813deb73de1cea9
Source dataset
uspto-grants-1992_08
Patent number
US05140038

Reaction notes

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