Acetic Acid → HCID 14208609, compound

HRID 845187Notes

Reaction equation

HRID 845187 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][C:4]([C:8]2[S:9][CH:10]=[CH:11][C:12]=2[S:13]([NH2:16])(=[O:15])=[O:14])=[CH:3]1.C1[CH2:27][CH2:26][N:25]2[C:20](=[N:21][CH2:22]CC2)CC1.[OH2:28].[C:29](O)(=O)C.[C:33](#[N:35])[CH3:34]>>[CH3:34][C:33]1[CH:29]=[C:26]([CH3:27])[N:25]=[C:20]([NH:21][C:22]([NH:16][S:13]([C:12]2[CH:11]=[CH:10][S:9][C:8]=2[C:4]2[CH2:5][CH2:6][CH2:7][C:2](=[O:1])[CH:3]=2)(=[O:15])=[O:14])=[O:28])[N:35]=1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 962WaterHCID 6342AcetonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 14208608HCID 14208608, compound

Product 1

HCID 14208609HCID 14208609, compound

Procedure

A mixture of the product from Example 2 (0.30 g, 1.17 mole) and N-(4,6-dimethylpyrimidin-2-yl)phenyl carbamate (0.30 g, 1.23 mmole) in acetonitrile (30 mL) was treated with DBU (184 μl, 1.23 mmole) at room temperature overnight. The solution was poured into water and acidified with acetic acid. The solid which precipitated was collected on a glass funnel and washed with water, butylchloride, and ether to yield 0.15 g white solid; m.p. 190°-192° C.; NMR (CDCl3)δ: 2.0-2.2 (m, 2H), 2.3-2.5 (m, with s at δ2.44, 8H), 2.7-2.8 (m, 2H), 6.25 (s, 1H), 6.77 (s, 1H), 7.36 and 7.66 (AB q, J=5.4 Hz, 2H); IR cm-1 (nujol): 1730, 1700 (shoulder at 1685 and 1675), 1605, 1550, 1170, 1140.

Workup

  1. customThe solid which precipitated
  2. customwas collected on a glass funnel
  3. washwashed with water, butylchloride, and ether

Sources & evidence

ORD record
ord-fd085077e8894d878e441318e60bb599
Source dataset
uspto-grants-1988_07
Patent number
US04756742

Reaction notes

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