N,N'-Dimethylthiourea → 3a-hydroxy-3-methyl-2-methylimino-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d]thiazole-6-carbonitrile

HRID 1275114Notes

Reaction equation

Br.[OH:2][C:3]12[C:14]3[CH:13]=[CH:12][C:11]([C:15]#[N:16])=[CH:10][C:9]=3[CH2:8][CH:7]1[S:6][C:5](=[N:17][CH3:18])[N:4]2[CH3:19].[Br:20]C1CC2C(=CC=C(C#N)C=2)C1=O.CNC(NC)=S>CC(C)=O>[BrH:20].[OH:2][C:3]12[C:14]3[CH:13]=[CH:12][C:11]([C:15]#[N:16])=[CH:10][C:9]=3[CH2:8][CH:7]1[S:6][C:5](=[N:17][CH3:18])[N:4]2[CH3:19].[OH:2][C:3]12[C:14]3[CH:13]=[CH:12][C:11]([C:15]#[N:16])=[CH:10][C:9]=3[CH2:8][CH:7]1[S:6][C:5](=[N:17][CH3:18])[N:4]2[CH3:19]

Participants

Conditions

Temperature: 0 °C

Procedure

3a-Hydroxy-3-methyl-2-methylimino-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d]thiazole-6-carbonitrile hydrobromide: 236 mg of 2-bromo-1-oxoindan-5-carbonitrile are dissolved in 10 ml of acetone and treated at 0-5° C. with 210 mg of N,N'-dimethylthiourea. The mixture is stirred at room temperature for 3 hours and at 0° C. for 1 hour. The reaction product is filtered off with suction, washed with acetone and dried in vacuo. The hydrobromide of 3a-hydroxy-3-methyl-2-methylimino-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d]thiazole-6-carbonitrile of melting point 282-284° C. (decomposition) is obtained.

Workup

filtrationThe reaction product is filtered off with suction
washwashed with acetone
customdried in vacuo

Sources & evidence

ORD record: ord-3d37b698b528407a82a7cac953e0d958
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06159996

Reaction notes

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