Dimethyl Sulfoxide → 2-(7-Bromo-9,9-diethyl-9H-fluoren-2-yl)-1,3-benzothiazole

HRID 1831858Notes

Reaction equation

[CH2:1]([C:3]1([CH2:19][CH3:20])[C:15]2[CH:14]=[C:13]([CH:16]=O)[CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][C:6]([Br:18])=[CH:7][CH:8]=2)[CH3:2].[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[SH:28].CS(C)=O>O>[Br:18][C:6]1[CH:5]=[C:4]2[C:9]([C:10]3[CH:11]=[CH:12][C:13]([C:16]4[S:28][C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=5[N:21]=4)=[CH:14][C:15]=3[C:3]2([CH2:1][CH3:2])[CH2:19][CH3:20])=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 195 °C

Procedure

A mixture of 9,9-diethyl-7-bromo-fluorene-2-carboxaldehyde (49.35 g., 0.15 mol.), 2-amino-thiophenol (20 ml. 0.187 mol., 1,25 eq.), and DMSO (110 ml) was heated in an oil bath to a bath temperature of 195° C., held there for 45 minutes, and then poured into water. The separated solids were collected, reslurried in 1:4 acetic acid-water (1000 ml.) filtered, and washed with water and dilute sodium bicarbonate solution. These solids, 80.05 g., were then reslurried in hot ethanol, (600 ml), cooled and filtered to get the benzothiazole product, 45.69 g., m.p. 133.6–135° C. An additional 6.6 g., m.p. 134.6–135.5° C., was obtained by chromatography of the ethanol filtrate. Total recovery was 52.29 g. (80.3% yield). Mass Spec: m/z 433, 435, (M+). Calculated for C24H20BrNS: C, 66.37; H, 4.64; Br, 18.40; N, 3.23; S, 7.37%. Found: C, 66.46; H, 4.52, Br, 18.54; N, 3.14; S, 7.19%.

Workup

customThe separated solids were collected
filtrationfiltered
washwashed with water and dilute sodium bicarbonate solution
temperaturecooled
filtrationfiltered

Sources & evidence

ORD record: ord-58205a8ed4ef49e5a2da6a74a5dd4857
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067674B1

Reaction notes

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