4-Chloro-2-nitrophenol → HCID 19012033, compound

HRID 1085268Notes

Reaction equation

HRID 1085268 reaction equation
Cl.[CH3:2][N:3]1[C:8]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=3[N+:26]([O-:28])=[O:27])[CH2:11][CH2:10]2)=[CH:7][C:6](=[O:29])[N:5]([CH3:30])[C:4]1=[O:31].ClC1C=CC(O)=C([N+]([O-])=O)C=1.CN1C(NCCNC(=O)C2C=CC([N+]([O-])=O)=CC=2)=CC(=O)N(C)C1=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:2][N:3]1[C:8]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=3[N+:26]([O-:28])=[O:27])[CH2:11][CH2:10]2)=[CH:7][C:6](=[O:29])[N:5]([CH3:30])[C:4]1=[O:31]

Participants

7

Reactant 5

HCID 69804-Chloro-2-nitrophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 20061162HCID 20061162, compound2×HCID 20061251HCID 20061251, compound2×

Product 1

HCID 19012033HCID 19012033, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Preparation of 1,3-dimethyl-6-{4-[3-(4-chloro-2-nitrophenoxy)propyl]piperazin-1-yl}-2,4(1H,3H)-pyrimidinedione hydrochloride (Compound 140) ##STR125## 0.80 g of 4-chloro-2-nitrophenol, 1.13 g of 1,3-dimethyl-6-[4-(3-hydroxypropyl)piperazin-1-yl}-2,4(1H,3H)-pyrimidinedione (Compound 139) and 1.21 g of triphenylphosphine were suspended in 15 ml of anhydrous tetrahydrofuran, followed by the addition of 0.80 g of diethyl azodicarboxylate. The resultant mixture was treated in a similar manner to Example 84-(2), thereby obtaining 1.43 g of 1,3-dimethyl-6-{4-[3-(4-chloro-2-nitrophenyloxy)propyl]piperazin-1-yl}-2,4(1H,3H)-pyrimidinedione as crystals.

Sources & evidence

ORD record
ord-59e88b0b47d5428dba7802d5b09bf256
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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