Benzenamine, N-sulfinyl- → HCID 178519023, compound

HRID 1653736

Reaction equation

HRID 1653736 reaction equation
[S:1](=NC1C=CC=CC=1)=O.[NH2:10][CH:11]([CH:15]1[CH2:20][N:19]([C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:18]=[N:17][CH2:16]1)[C:12]([NH2:14])=[O:13]>N1C=CC=CC=1>[C:22]1([C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:19]2[CH2:20][CH:15]([C:11]3[C:12]([OH:13])=[N:14][S:1][N:10]=3)[CH2:16][N:17]=[CH:18]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 70739Benzenamine, N-sulfinyl-HCID 20080439Amino(1-triphenylmethyl-1,4,5,6-tetrahydropyrimidin-5-yl)acetamide

Product 1

HCID 178519023HCID 178519023, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

N-Thionylaniline (2.6 mL, 23.2 mmol) is added to amino(1-triphenylmethyl-1,4,5,6-tetrahydropyrimidin-5-yl)acetamide (1.64 g, 4.1 mmol) suspended in pyridine (25 ml). After heating at 90° C. for 48 hours the pyridine is evaporated, and the black residue partitioned between chloroform and water. The aqueous layer is lowered to pH 5 (HCl) and chromatographed (Dowex-50W, 0.5N ammonium hydroxide) to yield the product as a brown solid 1.05 g (61%) that can be further purified by chromatography (silica, methanol) and converted to a white crystalline hydrochloride salt, ms m/z=426.

Workup

  1. customis evaporated
  2. customthe black residue partitioned between chloroform and water
  3. customchromatographed (Dowex-50W, 0.5N ammonium hydroxide)

Sources & evidence

ORD record
ord-679ec70d13a0433cb4955c17326c1153
Source dataset
uspto-grants-1995_04
Patent number
US05403845

Linked notes

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