3-Chlorobenzoic Acid → HCID 69520009, compound

HRID 1767737Notes

Reaction equation

HRID 1767737 reaction equation
ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.[Cl:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17]([OH:19])=O.C(N(CC)CC)C.C1(OC2C=CC=CC=2)C=CC=CC=1.[NH2:43][C:44]1[N:49]=[CH:48][C:47]([N+:50]([O-:52])=[O:51])=[CH:46][N:45]=1>C(OCC)(=O)C.C(OCC)C>[Cl:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17]([NH:43][C:44]1[N:49]=[CH:48][C:47]([N+:50]([O-:52])=[O:51])=[CH:46][N:45]=1)=[O:19]

Participants

8

Reactant 5

HCID 4473-Chlorobenzoic AcidHCID 7583Diphenyl EtherHCID 8471TriethylamineHCID 764905-Nitropyrimidin-2-amineHCID 94429Triphosgene

Product 1

HCID 69520009HCID 69520009, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

Triphosgene (5.63 g, 19 mmol) was added to an ice cold solution of 3-chlorobenzoic acid (17.76 g, 114 mmol) and triethylamine (16 ml, 114 mmol) in ethyl acetate (250 ml). The reaction was stirred for 15 min then 1 hour at ambient temperature. The mixture was filtered to remove triethylamine hydrochloride then concentrated in vacuo. Diphenyl ether (16 g) and 2-amino-5-nitropyrimidine (4 g, 28.6 mmol) were added, mixed and heated 20 hours at 150° C. The mixture was cooled and diluted with diethylether (100 ml). Collected of the solid by suction filtration yielded, 2-(N-3-chlorobenzoyl)amino-5-nitropyrimidine (7.94 g, 100% yield) as a beige solid:

Workup

  1. custom1 hour
  2. customat ambient temperature
  3. filtrationThe mixture was filtered
  4. customto remove triethylamine hydrochloride
  5. concentrationthen concentrated in vacuo
  6. additionmixed
  7. temperatureThe mixture was cooled
  8. filtrationCollected of the solid by suction filtration
  9. customyielded

Sources & evidence

ORD record
ord-0cf4998200b843f5b0046b3a1fa844e0
Source dataset
uspto-grants-2007_06
Patent number
US07235559B1

Reaction notes

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