Dibutylamine → HCID 14146303, compound

HRID 414311Notes

Reaction equation

C(N)(=S)C1C=CC=CC=1.[CH2:10]([C:12]1[S:16][C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:14][C:13]=1[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][CH2:32]Cl)=[CH:25][CH:24]=1)[CH3:11].[CH2:34]([NH:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:35][CH2:36][CH3:37]>>[CH2:10]([C:12]1[S:16][C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:14][C:13]=1[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][CH2:32][N:38]([CH2:39][CH2:40][CH2:41][CH3:42])[CH2:34][CH2:35][CH2:36][CH3:37])=[CH:25][CH:24]=1)[CH3:11]

Participants

Reactant 3

HCID 8148Dibutylamine

HCID 683563Thiobenzamide

HCID 14146287HCID 14146287, compound

Product 1

HCID 14146303HCID 14146303, compound

Procedure

The title compound was prepared according to Example 1, using p-hydroxybutyrophenone (20 g, 0.12 mol) in place of p-hydroxyacetophenone and 1-bromo-3-chloropropane (48 ml, 0.48 mol) to give 25 g (85% yield) of p-chloropropoxybutyrophenone as an oil. 1H NMR (CDCl3): δ7.92 (d, J=8.9 Hz, 2H), 6.91 (d, J=8.9 Hz, 2H), 4.15 (t, J=5.9 Hz, 2H), 3.73 (t, J=6.3 Hz, 2H), 2.87 (t, J=7.0 Hz, 2H), 2.23 (m, 2H), 1.78 (m, 2H), 0.99 (t, J= 7.0 Hz, 3H). Bromination (5 ml, 0.10 mol) followed by condensation with thiobenzamide (10 g, 73 mmol) of this product as described in Example 1 afforded 5-ethyl-4-(4-chloropropoxyphenyl)-2-phenylthiazole in 48% yield (15 g) as a white solid, mp 117°-119° C. Treatment of this product (5.1 g, 11 mmol) with dibutylamine in accordance with Example 1 gave 4.4 g (83% yield) of the free base of the title compound which was converted to the HCl salt, mp 128°-131° C. IR(KBr): 3400, 2610, 1620 cm-1, MS: 451(MH+). 1H NMR (CD3OD): δ7.96-7.02 (m, 9H), 4.12 (t, J=5.8 Hz, 2H), 3.38-2.76 (m, 8H), 2.20 (m, 2H), 1.75-1.18 (m, 14H), 0.91 (m, 3H).

Sources & evidence

ORD record: ord-fe014e59e43a407186b408b002976d8c
Source dataset: uspto-grants-1988_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04791200

Reaction notes

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