4,5,6,7-Tetrahydro-1-benzothiophen-4-amine → N-(4,5,6,7-Tetrahydro-1-benzothiophen-4-yl)urea

Reaction equation

[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]([NH2:10])[CH2:7][CH2:8][CH2:9][C:2]1=2.[C:11]([NH:19][C@H](C(O)=O)CCC(O)=O)(=[O:18])C1C=CC=CC=1>>[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]([NH:10][C:11]([NH2:19])=[O:18])[CH2:7][CH2:8][CH2:9][C:2]1=2

Participants

Reactant 2

HCID 42163724,5,6,7-Tetrahydro-1-benzothiophen-4-amine

HCID 11345724N-Benzoyl-L-glutamic acid

Product 1

HCID 13036998N-(4,5,6,7-Tetrahydro-1-benzothiophen-4-yl)urea

Procedure

Similarly, the salt of (+)-4,5,6,7-tetrahydrobenzo[b]thiophen-4-amine and (S)-(-)-N-benzoyl glutamic acid is treated in the above manner to afford (+)-4,5,6,7-tetrahydrobenzo[b]thien-4-ylurea, melting point 218° C. to 220° C.; [α]58925 +60°, [α]436 +149.8°, [α]365 +272.5°.

Sources & evidence

ORD record: ord-1a0fed9db15246a788375828d5c1207b
Source dataset: uspto-grants-1979_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04156670

Reaction notes

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